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Synfacts 2006(12): 1271-1271
DOI: 10.1055/s-2006-955610
DOI: 10.1055/s-2006-955610
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
Diastereoselective Synthesis of anti-1,2-Diols from α-Silyloxyaldehydes
K. Sa-Ei, J. Montgomery*
University of Michigan, Ann Arbor, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200612/lookinside/thumbnails/10.1055-s-2006-955610-1.jpg)
Significance
Allylic 1,2-diols are interesting and useful intermediates, for instance, in the synthesis of complex natural products. This reaction offers an elegant and attractive method for the diastereoselective preparation of anti-1,2-diols with an allylic double bond starting from readily available chiral α-silyloxyaldehydes. Very good regioselectivity together with high diastereoselectivity is observed for this process. Various internal alkynes undergo this reaction, giving rise to a variety of available products. The use of silylalkynes followed by the protodesilylation allows the preparation of allylic alcohols with disubstituted double bonds.