Stereoselectivity of the Radical Reductive Alkylation of Enamines: Importance of the Allylic 1, 3??Strain Model

S Schubert, P Renaud, PA Carrupt…

Index: Schubert, Serge; Renaud, Philippe; Carrupt, Pierre-Alain; Schenk, Kurt Helvetica Chimica Acta, 1993 , vol. 76, p. 2473 - 2489

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Citation Number: 29

Abstract

Abstract Radical addition to enamines using Bu 3 SnH as reducing agent are reported (Schemes 2 and 4). The diastereoselectivity of these reactions was examined in different systems (Tables 1 and 2). Enamines derived from cyclic ketones such as cyclohexanone were alkylated with high diastereoselectivity with preferential formation of the cis- disubstituted cycloalkanes. In acyclic systems such as enamines derived from ...