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Regio- and chemoselective conjugate 1,4-reduction of α-oxoketene dithioacetals with sodium borohydride and sodium cyanoborohydride

✍ Scribed by Ch. Srinivasa Rao; R.T. Chakrasali; Hiriyakkanavar Ila; Hiriyakkanavar Junjappa

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 662 KB
Volume: 46
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89784-2

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✦ Synopsis

Theor-oxoketene dithioacetals 1. are shown to undergo conjugate 1,4-reduction in highly regio-and chemoselective manner with sodium borohydride in acetic acid to afford the corresponding B-oxodithioacetals 5 in good yields. These results have been rationalized according to HSAB principle in terms of 'hard soft affinity inversion' concept. The reduction of 1 with sodium cyanoborohydride also proceeds in 1,4-conjugate addition-elimination manner to afford the corresponding vinylogous thiolesters 5 in good yields.

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