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Acceptor/Acceptor‐Substituted Diazo Reagents for Carbene Transfers: Cobalt‐Catalyzed Asymmetric Z‐ Cyclopropanation of Alkenes with α‐Nitrodiazoacetates
Author(s) -
Zhu Shifa,
Perman Jason A.,
Zhang X. Peter
Publication year - 2008
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.200803857
Subject(s) - cyclopropanation , diazo , cyclopropane , porphyrin , catalysis , acceptor , cobalt , carbene , chemistry , electron acceptor , reagent , combinatorial chemistry , medicinal chemistry , organic chemistry , physics , condensed matter physics , ring (chemistry)
Surprisingly cis ‐tematic! The cobalt(II) complex of a D 2 ‐symmetric chiral porphyrin is an effective catalyst for asymmetric cyclopropanation with α‐nitrodiazoacetates (see scheme). The catalytic system is general and suitable for electron‐sufficient, ‐neutral, and ‐deficient alkenes, forming the corresponding cyclopropane nitroesters in high yields. In addition to high diastereo‐ and enantioselectivity, the catalytic process exhibits atypical Z selectivity.