syn-Selective Reformatsky-Type Reaction of α-Silyl-α-stannylacetic Esters with Aldehydes: Stereoselective Synthesis of (E)- and (Z)-α,β-Unsaturated Esters

Shuji Akai; Yasunori Tsuzuki; Satoshi Matsuda; Shinji Kitagaki; Yasuyuki Kita

doi:10.1055/s-1991-20921

Synlett 1991; 1991(12): 911-912
DOI: 10.1055/s-1991-20921

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syn-Selective Reformatsky-Type Reaction of α-Silyl-α-stannylacetic Esters with Aldehydes: Stereoselective Synthesis of (E)- and (Z)-α,β-Unsaturated Esters

Shuji Akai^* , Yasunori Tsuzuki, Satoshi Matsuda, Shinji Kitagaki, Yasuyuki Kita

^*Faculty of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565, Japan

Abstract

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α-(tert-Butyldimethylsilyl)-α-(tributylstannyl)acetic esters 3, prepared in situ by the addition of alkoxytributylstannanes 2 to tert-butyldimethylsilylketene (1), reacted with aldehydes 4 in the presence of titanium(IV) chloride to give β-hydroxy-α-silyl esters 5 with high syn-selectivity in good overall yield. Stereocontrolled elimination of 5 gave possible entry to both (E)- and (Z)-α,β-unsaturated esters 6 depending on conditions used.

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