Vitamin B12 Derivatives as Natural Asymmetric Catalysts: Enantioselective Cyclopropanation of Alkenes

Ying Chen, X. Peter Zhang

Research output: Contribution to journalArticlepeer-review

Abstract

Vitamin B12 derivatives were found for the first time to be general and efficient catalysts for asymmetric cyclopropanation of alkenes with ethyl diazoacetate (EDA). Among several common derivatives, aquocobalamin (B12a) was shown to be the most effective catalyst for a variety of alkenes, providing cis-dominant cyclopropanes in excellent yields and moderate enantioselectivity. Reactivity studies under different conditions suggest that the active species in the proposed catalytic cycle is the base-on cob(II)alamin (B12r) that is generated possibly via in situ reduction of B 12a by EDA.

Original languageEnglish (US)
Pages (from-to)2431-2435
Number of pages5
JournalJournal of Organic Chemistry
Volume69
Issue number7
DOIs
StatePublished - Apr 2 2004

ASJC Scopus subject areas

  • Organic Chemistry

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