2011Organic LettersRequires access

Chiral Brønsted Acid Catalysis for Enantioselective Hosomi−Sakurai Reaction of Imines with Allyltrimethylsilane

Norie Momiyama, Hayato Nishimoto, Masahiro Terada

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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.

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What this paper is about

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.

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Available 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.

Key concepts: Chemistry, Enantioselective synthesis, Brønsted–Lowry acid–base theory, Catalysis, Organic chemistry, Combinatorial chemistry

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