Asymmetric cyclopropanation of olefins catalyzed by a chiral cobalt(II) porphyrin

Original Article

JOURNAL 807

Organic Communications

VOLUME & ISSUE

Year: 2017 Issue: 2 April-June

PAGES

p.79 - 89

DOI ADDRESS

http://doi.org/10.25135/acg.oc.11.17.04.019

STATISTICS

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AUTHORS

Albrecht Berkessel, Erkan Ertürk and Jörg M. Neudörfl

GRAPHICAL ABSTRACT

ABSTRACT

The cobalt(II) complex of the Halterman porphyrin, 5,10,15,20-tetrakis[(1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-yl]porphyrinato cobalt(II) [Co(por*)], was synthesized and its structure was identified by X-ray analysis. Up to 80:20 trans:cis diastereomeric ratio and 82% ee were achieved in the cyclopropanation of styrene with ethyl diazoacetate by using this cobalt(II) porphyrin complex as catalyst.

KEYWORDS

Asymmetric catalysis
cyclopropanation
cobalt
porphyrin
ethyl diazoacetate