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Scientific article
English

Construction of Bicyclo[3.2.1]octanes with Four Stereogenic Centers by Organocatalytic Domino Michael/Aldol Reaction

Published inOrganic letters, vol. 16, no. 20, p. 5242-5245
Publication date2014
Abstract

An enantio- and diastereoselective organocatalytic domino Michael/Aldol reaction for the direct preparation of synthetically and medicinally relevant bicyclo[3.2.1]octane derivatives with four stereogenic centers, including two quaternary carbons, has been described. The reaction tolerates a large variety of substituents on β,γ-unsaturated 1,2-ketoesters and cyclic 1,3-ketoesters. It allows for the formation of various bicyclo[3.2.1]octanes in good yields (53–98%), diastereoselectivities (1:1 to 5:1 dr), and enantioselectivities (up to 95:5 ee).

Citation (ISO format)
LEFRANC, Alice, GREMAUD, Ludovic, ALEXAKIS, Alexandre. Construction of Bicyclo[3.2.1]octanes with Four Stereogenic Centers by Organocatalytic Domino Michael/Aldol Reaction. In: Organic letters, 2014, vol. 16, n° 20, p. 5242–5245. doi: 10.1021/ol502171h
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ISSN of the journal1523-7052
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Creation11/03/2014 3:28:00 PM
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