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Asymmetric Synthesis of Aminocyclopropanes and N ‐Cyclopropylamino Alcohols Through Direct Amidocyclopropanation of Alkenes Using Chiral Organozinc Carbenoids
Author(s) -
Bégis Guillaume,
Cladingboel David E.,
Jerome Laure,
Motherwell William B.,
Sheppard Tom D.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200801033
Subject(s) - carbenoid , chemistry , cyclopropanation , enantioselective synthesis , stereoselectivity , indene , cyclopropane , yield (engineering) , triethyl orthoformate , chirality (physics) , organic chemistry , chiral auxiliary , stereochemistry , catalysis , rhodium , metallurgy , quark , ring (chemistry) , materials science , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model
Chiral N ‐(diethoxymethyl)oxazolidinones, prepared from the corresponding oxazolidinones by heating in triethyl orthoformate, can be used as organozinc carbenoid precursors for the direct enantioselective amidocyclopropanation of alkenes. The reaction is successful with a wide range of oxazolidinones and alkenes and proceeds with moderate to excellent yield and stereoselectivity. In most cases the trans / exo amidocyclopropane product is favoured, although certain cyclicalkenes such as indene favour the formation of the endo cyclopropane. The products can be readily elaborated to produce cyclopropylamino alcohols and amino acids.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)