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Reductive Alkylation of Enamines with Chloromethyl p ‐Tolyl Sulfone via a Radical Chain Process
Author(s) -
Renaud Philippe,
Schubert Serge
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199004331
Subject(s) - enamine , chemistry , steric effects , alkylation , cyclohexane , sulfone , selectivity , medicinal chemistry , organic chemistry , catalysis
Cyclic cnamines can be alkylatcd diastereoselectively with chloromethyl p ‐tolylsulfone . The cis ‐selectivity of this radical reaction is especially striking in the formation of cyclohexane derivatives such as 1 (>95%). The rate at which p ‐tolylsulfonylmethyl radical adds to the enamine is a function both of its donor characteristics and of steric factors.