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Synfacts 2009(6): 0676-0676  
DOI: 10.1055/s-0029-1216773
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Shi Epoxidation-Reduction Sequence toward Differentiated trans-1,2-Diols

Contributor(s): Benjamin List, Corinna Reisinger
S. M. Lim, N. Hill, A. G. Myers*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

Myers and co-workers have developed a synthetic route to optically active mono­silyl-protected trans-1,2-diols 3 via Shi asymmetric epoxidation of silyl enol ethers 1 followed by a regio- and stereospecific reduction of silyloxy epoxides 2 with BH3˙THF. Alternatively, AlMe3 or higher alkylides can be added to intermediates 2. tert-Butyldiphenylsilyl (TBDPS) ethers 1 proved particularly applicable due to the comparatively high stability of the corresponding silyloxy epoxides 2.