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Title

Stereoselectivity of the radical reductive alkylation of enamines - importance of the allylic 1,3-strain model

Authors
Schubert, S.
Renaud, P.
Schenk, K.
Published in Helvetica Chimica Acta. 1993, vol. 76, no. 7, p. 2473-2489
Abstract Radical addition to enamines using Bu3SnH 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 propiophenone and diethyl ketone, moderate to high stereoselectivities were observed in the H-abstraction step. A model based principally on minimization of allylic 1,3-strain (A1,3 strain) was deduced from the experimental results and semi-empirical (AM1) calculations
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SCHUBERT, S. et al. Stereoselectivity of the radical reductive alkylation of enamines - importance of the allylic 1,3-strain model. In: Helvetica Chimica Acta, 1993, vol. 76, n° 7, p. 2473-2489. https://archive-ouverte.unige.ch/unige:9976

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Deposited on : 2010-08-06

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