Addition of water to zinc triflate promotes a novel reaction: stereoselective Mannich-type reaction of chiral aldimines with 2-silyloxybutadienes.

J Org Chem

Department of Chemistry, The National Defense Academy, 1-10-20 Hashirimizu, Yokosuka 239-8686, Japan.

Published: June 2003

A novel stereoselective Mannich-type reaction of chiral aldimines with 2-silyloxybutadienes in the presence of zinc triflate and water has been achieved. The diastereoselectivities of the products were 74-90% de, and no cycloadducts were detected. Classical Mannich-type products were also obtained by using zinc triflate and water with high diastereoselectivities.

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http://dx.doi.org/10.1021/jo0300338DOI Listing

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