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Comparative enantiocontrol with allyl phenyldiazoacetates in asymmetric catalytic intramolecular cyclopropanation
Author(s) -
Doyle Michael P.,
Hu Wenhao,
Weathers Thomas M.
Publication year - 2003
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10219
Subject(s) - chemistry , cyclopropanation , intramolecular force , diazo , steric effects , alkene , catalysis , medicinal chemistry , decomposition , organic chemistry , stereochemistry
Dirhodium(II) azetidinone‐carboxylates are effective asymmetric catalysts for diazo decomposition of allyl diazoacetates and their subsequent intramolecular cyclopropanations. The effect of alkene substituents on enantiocontrol has been examined and modest selectivities have been achieved. Steric influences from substituents on the diazo carbon are seen to diminish enantioselectivities. Chirality 15:369–373, 2003. © 2003 Wiley‐Liss, Inc.