Diastereoselective and enantioselective cyclopropanation of alkenes catalyzed by cobalt porphyrins

Lingyu Huang, Ying Chen, Guang Yao Gao, X. Peter Zhang

Research output: Contribution to journalArticlepeer-review

Abstract

Cobalt(II) porphyrin complexes were shown to be general and efficient catalysts for selective cyclopropanation of alkenes with ethyl diazoacetate (EDA). The catalytic system can operate with alkenes as limiting reagents, requiring only stoichiometric amounts of EDA. The protocol is performed in one-pot fashion without the need of slow addition of EDA. The diastereoselectivity of the current system can be tuned by using different porphyrin ligands or additives, giving either trans- or cis-dominant cyclopropanes. The asymmetric cyclopropanation was also demonstrated with the use of chiral cobalt porphyrin complexes.

Original languageEnglish (US)
Pages (from-to)8179-8184
Number of pages6
JournalJournal of Organic Chemistry
Volume68
Issue number21
DOIs
StatePublished - Oct 17 2003

ASJC Scopus subject areas

  • Organic Chemistry

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