Asymmetric Aldol-Tishchenko Reaction of Sulfinimines

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Abstract

Methods for the preparation of 1,3-amino alcohols and their derivatives containing two stereogenic centers usually involve a two-step installation of the chiral centers. An aldol-Tishchenko reaction of chiral sulfinimines which involves the first reported reduction of a C=N in this type of reaction is described. Two and even three chiral centers can be installed in one synthetic step, affording anti-1,3-amino alcohols in good diastereo- and enantioselectivity.

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Foley, V. M., McSweeney, C. M., Eccles, K. S., Lawrence, S. E., & McGlacken, G. P. (2015). Asymmetric Aldol-Tishchenko Reaction of Sulfinimines. Organic Letters, 17(22), 5642–5645. https://doi.org/10.1021/acs.orglett.5b02919

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