Chiral Brønsted acid catalysis for enantioselective Hosomi-Sakurai reaction of imines with allyltrimethylsilane

Norie Momiyama; Hayato Nishimoto; Masahiro Terada

doi:10.1021/ol200595b

Chiral Brønsted acid catalysis for enantioselective Hosomi-Sakurai reaction of imines with allyltrimethylsilane

Org Lett. 2011 Apr 15;13(8):2126-9. doi: 10.1021/ol200595b. Epub 2011 Mar 24.

Authors

Norie Momiyama¹, Hayato Nishimoto, Masahiro Terada

Affiliation

¹ Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578, Japan. momiyama@m.tohoku.ac.jp

PMID: 21434633
DOI: 10.1021/ol200595b

Abstract

The chiral Brønsted acid (1b or 1c) has been shown to initiate the Hosomi-Sakurai reaction of imines with excellent enantioselectivities. The combined Brønsted acid system has been developed to offer a new class of chiral Brønsted acid catalysis. The present system proceeds through regeneration of the chiral Brønsted acid by proton transfer from additional Brønsted acid to silylated chiral Brønsted acid, a newly elucidated mechanism for the role of the additional Brønsted acid.