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Enantioselective [3+2] cycloaddition of azomethine

ylides and aldehydes via Ni/bis(oxazoline)-catalyzed
Cite this: Chem. Commun., 2017,
53, 5661 ring opening of N-tosylaziridines through a
Received 18th April 2017,
Accepted 3rd May 2017
chirality transfer approach†
DOI: 10.1039/c7cc02906c Xingxing Wu,a Wei Zhou,a Hai-Hong Wu*a and Junliang Zhang *ab
rsc.li/chemcomm

A diastereo- and enantioselective formal [3+2] cycloaddition of to access nitrogen heterocycles.7 Carrie8a and Johnson8b achieved
N-tosylaziridines and aldehydes catalyzed by a Ni(II)-bisoxazoline the selective C–C bond heterolysis of the aziridine promoted by a
complex has been accomplished. The 1,3-oxazolidine products are stoichiometric amount of a Lewis acid. Engels9 investigated C–N
obtained with high diastereoselectivity, good yields (up to 99%) and vs. C–C bond breakage of the aziridine8 through computational
high ee values (up to 96% ee). The challenging long distant stereo- calculations, which provided insight into the mechanism of
center control is achieved by a chirality transfer approach. the two different ring-opening patterns. Very recently, Feng has
realized an enantioselective [3+2] cycloaddition of N-tosylaziridines
The chiral 1,3-oxazolidine ring is the core structure of many and aldehydes via a relay catalytic approach.8h
natural products1a,b and an important structural motif in a Our laboratory is interested in the selective carbon–carbon
wide range of chiral pharmaceuticals,1c–e such as quinocarcin bond cleavage of aziridines.8c–e Previously, we8d successfully
and terazomine.1d Particularly, the importance of this class of achieved the diastereoselective synthesis of 1,3-oxazolidines by the
compounds is illustrated by their wide range of applications in Ni(II)-catalyzed [3+2] cycloaddition of aziridines with aldehydes.
asymmetric synthesis used as versatile auxiliaries.2 Recently, Herein, we demonstrate an enantioselective version of this trans-
the asymmetric catalysis with chiral 1,3-oxazolidine ligands has formation by the employment of a bisoxazoline (Box) derived
received wide attention, and achieved significant success in the nickel(II) complex as the catalyst (Fig. 1). Instead of extensive
alkylation and alkynylation of aldehydes,3a–c allylic alkylations,3d,e modification of the chiral ligands (usually with long synthetic
nitroaldol reactions, etc.3f,g However, to our surprise, general routes) to improve the enantioselectivities, our method employs a
synthetic methods for the preparation of chiral 1,3-oxazolidines chirality transfer approach with ‘‘designed’’ aziridine substrates
remain scarcely explored, despite their importance has been under a simple catalytic system. The desired 1,3-oxazolidines are
displayed in multiple disciplines.4 obtained in excellent yields and enantioselectivities.
Aziridines, the smallest N-containing heterocyclic compounds, Inspired by our previous preliminary result that Ni/indane-
have been extensively studied in organic synthesis.5 Their chem- Pybox could achieve moderate ee, we began to screen other
istry is characterized by the relatively high strain, which results in Pybox and Box ligands to test the enantioselective cycloaddition
the easy cleavage of the carbon–nitrogen bond under the catalysis of aziridine 1a10 with trimethoxybenzaldehyde (2a) (for details,
of Lewis acids to behave as a 1C, 3N-ylide.6 On the other hand, see Table S1 in the ESI†). Gratifyingly, the oxazolidine 3aa
under thermal or photochemical conditions, aziridines are also was obtained in good yield with 88% ee in the presence of
known to proceed through the C–C bond-breaking process to form in situ generated cationic nickel(II) catalysts from 5 mol% of
a 1C, 3C-ylide (azomethine ylide). As an active intermediate, it can Ni(ClO4)2
6H2O and 6 mol% of Bn-Box (L1)11 [Fig. 1a, eqn (1)].
be trapped by various dipolarophiles in 1,3-diploar cycloadditions However, under the same conditions, the reaction of 1a with
p-methoxybenzaldehyde (2b) afforded the corresponding product
a
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department
3ab with a much lower ee value (58% ee) [eqn (2)]. The sharp
of Chemistry, East China Normal University, Shanghai 200062, China. decrease in enantioselectivity may result from the fact that
E-mail: jlzhang@chem.ecnu.edu.cn the cycloaddition proceeded through a stepwise mechanism.
b
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic The electrophilic iminium carbon of the key azomethine ylide
Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China
is too far from the chiral center of the Box ligands, making it
† Electronic supplementary information (ESI) available: Experimental proce-
dures, mechanistic details, spectroscopic data and copies of 1H and 13C NMR
difficult to realize high enantio-induction for the newly formed
spectra. CCDC 895347 (3lc). For ESI and crystallographic data in CIF or other stereocenter. In the case of trimethoxybenzaldehyde (1a), the
electronic format see DOI: 10.1039/c7cc02906c substituent (OMe) on the meta position of the phenyl ring plays

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Table 1 Reaction optimizationa

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Entry R1 (1) L* Time (h) Yieldb (%) ee (%)

1 Me (1a) L1 3 3ac (83) 66
2 1a L2 3 3ac (87) 40
3 1a L3 3 3ac (89) 31
4 1a L4 3 3ac (58) 17
5 1a L5 24 3ac (46) 21
6 Et (1b) L1 3 3bc (99) 33
i
7 Pr (1c) L1 12 3cc (97) 81
8 Bn (1d) L1 12 3dc (65) 58
t
9 Bu (1e) L1 24 3ec ( ) —
10 CH2tBu (1f) L1 12 3fc (90) 93
11 1f L2 12 3fc (87) 88
12 1f L3 24 3fc (trace) n.d.
a
Reaction conditions: 1 (0.2 mmol), 2c (1.5 equiv.), Ni(ClO4)2/L (1/1.2,
Fig. 1 (a) Preliminary results on asymmetric [3+2] cycloaddition of aziridines. 5 mol%), and 100 mg of activated 4 Å MS in 2 mL of solvent at room
temperature. b Yield of isolated product. n.d. = not determined.
(b) Our proposed approaches (1 and 2) to improve the enantioselectivity
control. Ts = 4-toluenesulfonyl.

the catalysis of NiII/L1 (entry 10). Switching of the ligand to

a crucial role in the high selectivity, due to its repulsion with bisoxazolines L2 and L3 could not provide better results
the benzyl group of the ligand L1 (Fig. 1b, model 1). (Table 1, entries 11 and 12).
As there is an obvious steric effect for this transformation, The reactivity of a range of aziridines 1 was then examined,
we turned our attention to investigate a general catalyst system. affording oxazolidine products 3 in 77–99% yields with high
Aziridine 1a and simple p-methylbenzaldehyde 2c were then enantioselectivities under the optimized conditions. Aziridines
selected as the model substrates. The reaction proceeded smoothly with electron-donating groups (1g–h and 1i) at different positions on
in toluene to furnish the desired cycloadduct 3ac in 83% yield with the phenyl ring were smoothly transformed into the corresponding
a promising 66% ee under the catalysis of Ni(ClO4)2
6H2O/Bn-Box oxazolidines 3gc, 3hc and 3ic in 89–94% yields, with ee values
(L1) (Table 1, entry 1). The use of iPr-Box (L2), Ph-Box (L3) or ranging from 89 to 92% (Table 2, entries 2–4). Relatively higher ee
tBu-Box (L4) as the chiral ligand resulted in lower ee, and L4 values were obtained from the reactions of aziridines 1j–m bearing
caused a heavy decrease in yield due to the bulky steric effect electron-withdrawing groups on the phenyl ring, albeit with longer
(Table 1, entries 2–4). The indane-Pybox L5 led to a slow reaction time to achieve complete conversion (Table 2, entries 5–8).
transformation and only 46% yield with 21% ee was obtained For instance, the reaction of the p-nitrophenyl derived substrate 1j
(Table 1, entry 5). These results indicated that substituents on with 2c took 72 h to furnish 3jc in 77% yield with 96% ee (Table 2,
the Box ligand affected the reactivity and enantioselectivity entry 5). Aziridine with a naphthyl group (1n) provided the desired
significantly. Further optimization of the reaction conditions, product 3nc in 93% yield with 89% ee (entry 9). It is noteworthy that
including different solvents, Pybox ligands, temperatures, or substrate 1o with an easily removable nosyl group also proceeded
additives (such as O = PPh3, Ca(OCl)2, LiI, benzoic acid), failed facilely to give 3oc with excellent enantioselectivity (Table 2,
to give better results (see Tables S2 and S3, ESI†). entry 10). The absolute stereochemistry of the products was
To achieve high enantioselectivity with a broad substrate scope confirmed by the X-ray structure of optically active 3lc.12
without tedious modification of the chiral ligands, a chirality We next turned our attention to study the reaction scope
transfer approach was considered via the introduction of a bulky by variation of the aldehyde component, and the results are
ester group to realize the chirality information transfer from summarized in Table 3. In general, the electronic nature of the
the ligand to the newly formed stereocenter (Fig. 1b, model 2). aromatic aldehyde had a slight effect on the enantioselectivity.
A series of aziridines 1b–1f bearing different R1 groups including Both electron-deficient and electron-rich aldehydes afforded
Et (1b), iPr (1c), Bn (1d), tBu (1e), and CH2tBu (1f) were prepared the corresponding products with high enantioselectivities.
and tested (Table 1, entries 6–10). Gratifyingly, the outcomes However, in terms of the conversion, aldehydes with electron-
indeed supported our hypothesis. Aziridine 1f with a bulky donating groups on the phenyl ring worked better than those
ester group led to excellent yield and enantioselectivity under substituted with electron-withdrawing groups. For example, the

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Table 2 Study of the reaction scope by variation of aziridine component (Table 3, entries 10 and 11). The introduction of an a-substituent
on the a,b-unsaturated aldehydes led to better enantioselectivity.
For example, the reaction of E-2-methyl-2-butenal (2n) with an
a-methyl group gave a much higher enantioselectivity (87% ee)
than that with simple enal 2m (69% ee, Table 3, entries 12 and
13). Gratifyingly, cyclohex-1-enecarbaldehyde is also a compati-
Entry Ar Time (h) Yield (%) ee (%) ble substrate (3fo, 79% yield and 85% ee, Table 3, entry 14).
Published on 03 May 2017. Downloaded by Indian Institute of Technology Kanpur on 4/1/2024 2:17:32 PM.

1 Ph (1f) 12 3fc (90) 93

To demonstrate the potential synthetic utility and catalytic
2 4-iPrC6H4 (1g) 12 3gc (89) 89 efficiency of this method, a gram-scale reaction was performed
3 4-MeC6H4 (1h) 18 3hc (94) 92 [eqn (3)]. The reaction of 1f (4.01 g) with 2c proceeded smoothly
4 3-MeC6H4 (1i) 12 3ic (89) 92
5 4-NO2C6H4 (1j) 72 3jc (77) 96
with 2 mol% catalyst loading, yielding 4.28 g (85% yield) of
6 4-ClC6H4 (1k) 12 3kc (99) 94 oxazolidine 3fc as a single diastereoisomer with 93% ee. This
7 4-BrC6H4 (1l) 12 3lc (85) 95 result indicated that the catalyst loading could be reduced with
8 3-BrC6H4 (1m) 38 3mc (84) 92
9 2-Naphthyl (1n) 12 3nc (93) 89
no loss in reaction efficiency and selectivity.
10a Ph (1o) 60 3oc (78) 92
a
The N-Ts group was replaced by the N-Ns group. Ns = 4-nitrobenzene-
sulfonyl. (3)

reactions of 2a and 2b proceeded smoothly to give the desired

products in 88–91% yields with high ee values within 12 h
In summary, we have developed a catalytic diastereo- and
(Table 3, entries 1 and 2). When electron-deficient aryl aldehydes
enantioselective [3+2] cycloaddition of aziridines with aldehydes
were applied as the substrates, there was a significant drop in
involving azomethine ylides via a chirality transfer approach. Our
the reaction rate. Higher catalyst loading was required in these
strategy for remote chirality control provides an efficient method
cases, but to our delight, high ee values were still obtained
for the asymmetric construction of chiral 1,3-oxazolidines without
(Table 3, entries 6 and 7). This transformation could be readily
the need of tedious modification of chiral ligands. Mild conditions,
extended to heterocyclic aldehyde (2i) and other aryl aldehydes
readily available starting materials, commercially available bisox-
(2j), with the formation of the corresponding products 3fi in 94%
azoline as the chiral ligand, easy scale-up, as well as the high yield
yield with 88% ee and 3fj in 76% yield with 86% ee, respectively
and excellent enantioselectivity make this protocol synthetically
(Table 3, entries 8 and 9). a,b-Unsaturated aldehydes also worked
useful in organic synthesis. Further asymmetric reaction develop-
well to produce the corresponding cycloadducts with readily
ment with the chirality transfer approach and bioactivity study of
convertible olefins. For example, the reactions of cinnamaldehyde
chiral oxazolidines is in progress in our lab.
(2k) and its analogue 2l produced 82–93% yields of products
We are grateful to the 973 Program (2015CB856600), the
with excellent enantioselectivities (88% and 92% ee, respectively)
National Natural Science Foundation of China (21373088, 21425205,
and 21672067), and the Changjiang Scholars and Innovative
Research Team in University (PCSIRT) for financial support.
Table 3 Study of the reaction scope by variation of aldehyde component
Notes and references
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