Journal of the Chemical Society. Perkin transactions I p. 2813 - 2820 (1992)
Update date:2022-08-04
Topics:
Akai, Shuji
Tsuzuki, Yasunori
Matsuda, Satoshi
Kitagaki, Shinji
Kita, Yasuyuki
Silylketenes 1a, b reacted smoothly with alkoxystannanes 3 to give the corresponding α-silyl-α-stannylacetates 4 almost quantitatively.Treatment of 4 with TiCl4 caused selective cleavage of the C-Sn bond to bring about Reformatsky-type reaction with aldehydes 6 giving β-hydroxy-α-silyl esters 7.These two steps were carried out by one-pot operation, and variously substituted compounds 7 were obtained with high syn-selectivity (52-<*>96percent d.e.) in 41-89percent yields.A similar one-pot procedure starting from 1a-c, 3, and aldimines 11 also provided the corresponding β-amino-α-silyl esters 12 with excellent syn-selectivity (<*>96percent d.e. ) in 64-94percent yields.Stereocontrolled preparation of both (E)- and (Z)-α,β-unsaturated esters 8 and a syn-amino diol derivative 17 from syn-7 and syn-12, respectively, is also described.
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