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Diastereoselective alkylation of the ( + )‐ketopinic acid ketimine derived from benzylamine
Author(s) -
Deng JinGen,
Hu WenHao,
Liu GuiLan,
Mi AiQiao,
Jiang YaoZhong
Publication year - 1990
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19900080609
Subject(s) - chemistry , alkylation , benzylamine , diastereomer , electrophile , tsuji–trost reaction , halide , organic chemistry , lithium (medication) , medicinal chemistry , catalysis , allylic rearrangement , medicine , endocrinology
Alkylation of the ketimine 2 obtained from condensation of (+)‐ketopinic acid and benzylamine with a variety of alkylating agents gives the products whose trends in diastereomeric excesses (1 — 100% O.P.) appear to correlate with the structure and reactivity of electrophilic agents. Using excess n ‐butyl lithium and allylic or benzylic halides, β‐alkylation occured.
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