Asymmetric Organocatalytic Domino Michael/aldol Reactions: Enantioselective Synthesis of Chiral Cycloheptanones, Tetrahydrochromenones, and Polyfunctionalized Bicyclo[3.2.1]octanes

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2009 Apr 21

PMID 19378300

Citations 14

Authors

Magnus Rueping

Alexander Kuenkel

Francisco Tato

Jan W Bats

Affiliations

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Abstract

C'mon 1,2-dione: A new diastereo- and enantioselective Lewis base catalyzed domino Michael/aldol reaction converts alpha,beta-unsaturated aldehydes and 1,2-diones into chiral bicyclo[3.2.1]octane-6-carbaldehydes. The products are produced in good to excellent enantioselectivities (90-98 % ee) and can be transformed into bicyclic diols and triols. Additionally, a retro-aldol cyclization provides access to valuable tetrahydrochromenones (see scheme).

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