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Chemoselective and stereoselective addition of organocuprates to α-oxoketene dithioacetals

✍ Scribed by R.Karl Dieter; Jeffrey R. Fishpaugh; Louis A. Silks

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
223 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

The chemoselective and stereoselective addition of organocuprates to cyclic a-oxoketene dithioacetals affords predominately the E vinylogous thioesters.

An acyclic a-oxoketene dithioacetal affords the 2 vinylogous thioester stereoselectively.

The observed selectivities are dependent upon substrate structure and the organocopper reagent.

📜 SIMILAR VOLUMES

Regio- and chemoselective conjugate 1,4-
Regio- and chemoselective conjugate 1,4-reduction of α-oxoketene dithioacetals with sodium borohydride and sodium cyanoborohydride
✍ Ch. Srinivasa Rao; R.T. Chakrasali; Hiriyakkanavar Ila; Hiriyakkanavar Junjappa 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 662 KB

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