Issue 13, 2021

Organocatalytic stereoselective 1,6-addition of thiolacetic acids to alkynyl indole imine methides: access to axially chiral sulfur-containing tetrasubstituted allenes

Abstract

A chiral phosphoric acid-catalyzed enantioselective 1,6-conjugate addition of thiolacetic acid to alkynyl indole imine methide in situ formed from α-(3-indolyl) propargylic alcohol has been established, which enables the formation of axially chiral sulfur-containing tetrasubstituted allenes in generally high efficiency with stereoselectivity.

Graphical abstract: Organocatalytic stereoselective 1,6-addition of thiolacetic acids to alkynyl indole imine methides: access to axially chiral sulfur-containing tetrasubstituted allenes

Supplementary files

Article information

Article type
Research Article
Submitted
11 Mar 2021
Accepted
23 Apr 2021
First published
26 Apr 2021

Org. Chem. Front., 2021,8, 3469-3474

Organocatalytic stereoselective 1,6-addition of thiolacetic acids to alkynyl indole imine methides: access to axially chiral sulfur-containing tetrasubstituted allenes

Z. Wang, X. Lin, X. Chen, P. Li and W. Li, Org. Chem. Front., 2021, 8, 3469 DOI: 10.1039/D1QO00394A

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