Srinivasa Rao, Ch. ; Chakrasali, R. T. ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1990) Regio- and chemoselective conjugate 1,4-reduction of α-oxoketene dithioacetals with sodium borohydride and sodium cyanoborohydride Tetrahedron, 46 (6). pp. 2195-2204. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)89784-2
Abstract
The α-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 β-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 6 in good yields.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
ID Code: | 29961 |
Deposited On: | 23 Dec 2010 03:55 |
Last Modified: | 22 Feb 2011 04:58 |
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