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Two‐Step Synthesis of trans ‐2‐Arylcyclopropane Carboxylates with 98–100 % ee by the Use of a Phosphazene Base
Author(s) -
SolladiéCavallo Arlette,
DiepVohuule Ahn,
Isarno Thomas
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980703)37:12<1689::aid-anie1689>3.0.co;2-9
Subject(s) - sulfonium , deprotonation , phosphazene , enantioselective synthesis , cyclopropanation , diastereomer , base (topology) , alkylation , chemistry , salt (chemistry) , combinatorial chemistry , organic chemistry , stereochemistry , medicinal chemistry , catalysis , mathematics , ion , polymer , mathematical analysis
Only the axial diastereomer of sulfonium salts 2 are formed upon alkylation of 1 . Deprotonation of 2 results in ylides, which allow the highly enantioselective cyclopropanation of Michael systems. The chiral auxiliary 1 is recovered and can be reused.