Subscribe to RSS
Shi Epoxidation-Reduction Sequence toward Differentiated trans-1,2-Diols
S. M. Lim, N. Hill, A. G. Myers*
Harvard University, Cambridge, USA
25 May 2009 (online)
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.