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

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Published in Organic letters. 2014, vol. 16, no. 20, p. 5242-5245
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).
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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 https://archive-ouverte.unige.ch/unige:41533

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Deposited on : 2014-11-04

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