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Synfacts 2009(10): 1160-1160  
DOI: 10.1055/s-0029-1217943
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Substrate-Controlled Aldehyde Alkynylations

Contributor(s): Benjamin List, Lars Ratjen
K. Wadhwa, V. R. Chintareddy, J. G. Verkade*
Iowa State University, Ames, USA
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

A proazaphosphatrane 1 mediated aldehyde alkynylation is reported. In this transformation the nature of the aldehyde regulated the outcome of the reaction, regardless of the alkyne substitution pattern. Whereas electron-rich or neutral aldehydes provided the expected alkynylation products 2, electron-deficient aldehydes underwent further reaction, furnishing Morita-Baylis-Hillman (MBH) type products 3. Presumably the latter pathway is enabled by an allene intermediate 4 which could be isolated from the crude material.