ChemComm
Communication
Shanghai Jiao Tong University (SJTU). We thank Prof. Tsuneo
Imamoto and Dr Masashi Sugiya for helpful discussions and
the Instrumental Analysis Center of SJTU for determination
of HRMS.
Notes and references
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a
Scheme 3 Scope of substrates. Conditions: 3 (0.05 mol LÀ1), (R)-2a
b
(10 mol%), t-AA (1.5 mL), 0 1C, 36 h. Conversions were determined by
1H NMR. Ees were determined by HPLC with chiral columns.
c
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C. Concellon, J. E. Thomson, C. D. Campbell, A. M. Z. Slawin and
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Scheme 4 A plausible mechanism.
hindrance between the groups of OR1 and the lactone and also
between the oxygen in the carbonyl group and R2. TS-2 is favored
for its higher stability. Significant steric hindrance only exists
between OR1 and R2. No significant steric interaction should occur
between the oxygen in the carbonyl group and the lactone in TS-2.
The minor isomer (S)-4 and the major isomer (R)-4 were obtained
via the disfavored TS-1 and favored TS-2, respectively. Catalyst (R)-2
is released to take part in the next catalytic cycle.
To summarize, we have examined the performance of chiral
imidazole nucleophilic catalysts in the enantioselective Black
rearrangement for the first time. Using the readily prepared 5 (a) T. A. Duffey, S. A. Shaw and E. Vedejs, J. Am. Chem. Soc., 2009,
131, 14; (b) M. Ismail, H. V. Nguyen, G. Ilyashenko, M. Motevalli and
C. J. Richards, Tetrahedron Lett., 2009, 50, 6332; (c) J. E. Delorbe,
S. Y. Jabri, S. M. Mennen, L. E. Overman and F.-L. Zhang, J. Am. Chem.
catalyst Acyloxy-DPI, a wide range of products with different
substituted groups was obtained with up to 88% ee. A plausible
mechanism for the high enantioselectivity was proposed.
This work was partially supported by the National Natural
Science Foundation of China (21172143, 21172144, 21202096,
and 21232004), Nippon Chemical Industrial Co. Ltd, and
Soc., 2011, 133, 6549; (d) D. Uraguchi, K. Koshimoto and T. Ooi,
J. Am. Chem. Soc., 2012, 134, 6972.
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(b) M. Suginome and G. C. Fu, Chirality, 2000, 12, 318; (c) J. G.
Seitzberg, C. Dissing, I. Søtofte, P. Norrby and M. Johannsen, J. Org.
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