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Published March 16, 2005 | Supplemental Material
Journal Article Open

Enantioselective Organocatalytic Cyclopropanations. The Identification of a New Class of Iminium Catalyst Based upon Directed Electrostatic Activation


A new method for enantioselective organocatalytic cyclopropanation is described. This study outlines the identification of a new class of iminium catalyst based on the concept of directed electrostatic activation (DEA). This novel organocatalytic mechanism exploits dual activation of ylide and enal substrates through a proposed electrostatic activation and stereodirected protocol. Formation of trisubstituted cyclopropanes with high levels of enantio- and diastereoinduction is accomplished for a variety of α,β-unsaturated aldehydes and sulfonium ylides. In addition, mechanistic studies have found that this cyclopropanation reaction exhibits enantioselectivity and reactivity profiles that are in accord with the proposed DEA step.

Additional Information

© 2005 American Chemical Society. Received 1 December 2004. Published online 18 February 2005. Published in print 1 March 2005. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Amgen and Merck. R.K.K. is grateful for an NIH postdoctoral fellowship (5 F32 GM 066595-02).

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Supplemental Material - ja042774bsi20050118_014247.pdf


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