SYNTHESIS OF 2-VINYL-1,3-DIOLS VIA HIGHLY STEREOSELECTIVE REDUCTION OF 2-VINYL ALDOLS USING TRIMETHYLSILYL STEREO-DIRECTING GROUP

Article abstract of DOI:10.1016/S0040-4039(00)85440-4

Stereo-defined 2-vinyl-1,3-diols are synthesized by the reduction of aldol derivatives bearing α-trimethylsilylvinyl group at C(2) (LiBEt3H/THF, -78 deg C), which proceeds highly stereoselectively to give 1,2-syn isomer as the sole product.