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Radical Cyclization/β-Elimination Tandem Reactions: Enantiopure Sulfoxides as Temporary Chiral Auxiliaries.

作者信息

Lacôte Emmanuel, Delouvrié Bénédicte, Fensterbank Louis, Malacria Max

机构信息

Laboratoire de Chimie Organique de Synthèse, associé au CNRS, Université Pierre et Marie Curie, 4, place Jussieu, Tour 44-54, Case 229 F-75252 Paris Cedex 05 (France), Fax: (+33) 1-44-27-73-60.

出版信息

Angew Chem Int Ed Engl. 1998 Aug 17;37(15):2116-2118. doi: 10.1002/(SICI)1521-3773(19980817)37:15<2116::AID-ANIE2116>3.0.CO;2-L.

DOI:10.1002/(SICI)1521-3773(19980817)37:15<2116::AID-ANIE2116>3.0.CO;2-L
PMID:29711040
Abstract

Alkylidene-substituted cyclopentane derivatives are formed in high enantiomeric purity by the reaction shown below. A highly diastereoselective radical cyclization is followed by elimination of a β-sulfinyl radical. Interestingly, the addition of the Lewis acid methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) totally reverses the stereochemical outcome of the reaction. E=CO Me.

摘要

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