Issue 25, 2016

Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde

Abstract

A highly diastereo- and enantioselective [3 + 3] annulation of donor–acceptor cyclopropanes with mercaptoacetaldehyde has been developed. In the presence of a N,N′-dioxide–Sc(III) complex as the catalyst, a number of aromatic substituted cyclopropyl ketones reacted with mercaptoacetaldehyde smoothly, providing the corresponding chiral tetrahydrothiopyranols in moderate yields with excellent ee (up to 99% ee) and dr values (up to >19 : 1).

Graphical abstract: Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde

Supplementary files

Article information

Article type
Communication
Submitted
01 May 2016
Accepted
18 May 2016
First published
18 May 2016

Org. Biomol. Chem., 2016,14, 5914-5917

Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde

X. Fu, L. Lin, Y. Xia, P. Zhou, X. Liu and X. Feng, Org. Biomol. Chem., 2016, 14, 5914 DOI: 10.1039/C6OB00948D

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