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Review | Special issue | Vol 28, No. 2, 1989, pp.1229-1247
Published online, 1st January, 1970
DOI: 10.3987/REV-88-SR5
Asymmetric Induction in the Intramolecular Conjugate Addition of γ- or δ-Carbamoyloxy-α,β-unsaturated Esters. A New Method for Diastereoselective Amination and Divergent Syntheses of 3-Amino-2,3,6-Trideoxyhexoses

Masahiro Hirama and Shô Itô*

*Department of Chemistry, Graduate School of Science, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Prominent 1,2- and 1,3-asymmetric induction in the intramolecular conjugate addition of γ- or δ-carbamoyloxy-α, β-unsaturated esters provides a new method for diastereoselective amination of acyclic olefinic systems, which has been applied to stereocontrolled divergent syntheses of 3-amino-2,3,6-trideoxyhexoses. Factors controlling the stereochemistry are discussed, and related cyclizations are also described.