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Synlett 1992; 1992(1): 81-83
DOI: 10.1055/s-1992-21274
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Acyclic Diastereoselection via Claisen Rearrangement with Boron Enolates. Chelation Control of Enolate Geometry

Taeboem Oh* , Zbigniew Wrobel, Paul N. Devine
  • *Department of Chemistry, State University of New York, Binghamton, New York 13902-6000, USA
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Publication Date:
18 September 2002 (online)

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The Ireland-Claisen rearrangement of a variety of O-protected 2-butenyl glycolates via chelated boron and tin triflates to give after esterification methyl 2-methoxy/benzyloxy-3-methyl-4-pentenoates is described. Diastereoselectivities as high as 99.5% were observed. The rates of rearrangement involving boron enolates are higher than those involving silyl ketene acetals or lithium enolates.