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Efficient Construction of α‐Spirocyclopropyl Lactones: Iridium–Salen‐Catalyzed Asymmetric Cyclopropanation
Author(s) -
Ichinose Masami,
Suematsu Hidehiro,
Katsuki Tsutomu
Publication year - 2009
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/anie.200805527
Subject(s) - cyclopropanation , iridium , regioselectivity , carbene , chemistry , catalysis , selectivity , medicinal chemistry , hydrolysis , stereochemistry , organic chemistry
Three‐ and seven‐membered rings were constructed by the title reaction of terminal olefins with vinyldiazolactone as a carbene source, the seven‐membered rings upon subsequent hydrolysis and Cope rearrangement when 1,3‐dienes were used (see example). The α‐spirocyclopropyl lactones were formed with high E ( trans ) selectivity and high enantioselectivity, and cyclopropanation occurred at the terminal double bond in 1,3‐dienes with excellent regioselectivity.