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Synthesis 2006(10): 1697-1700  
DOI: 10.1055/s-2006-926450
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Trans Effect on Cobalt Porphyrin Catalyzed Asymmetric Cyclopropanation

Ying Chen, X. Peter Zhang*
Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600, USA
Fax: +1(865)9743454; e-Mail: pzhang@utk.edu;
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Publication History

Received 16 February 2006
Publication Date:
27 April 2006 (online)

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Abstract

A significant trans effect of potential coordinating additives was found in asymmetric cyclopropanation catalyzed by Co(II) complexes of D 2 -symmetric chiral porphyrins [Co(1)]. Among different additives, substoichiometric amounts of DMAP resulted in substantial increases in both diastereoselectivity and enantioselectivity. A related solvent effect on the catalytic system was also observed.

Key words

cyclopropanation - chiral porphyrins - cobalt - trans effect - asymmetric catalysis

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