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Synlett 2001; 2001(Special Issue): 0977-0979
DOI: 10.1055/s-2001-14638
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Allylic Dithioacetal as a Propene-1,3-Zwitterion Synthon. Regioselective Conversion of C-S Bonds in Allylic Dithioacetals into C-C Bonds

Chao-Cheng Chiang* , Tien-Yau Luh
  • *Department of Chemistry, National Taiwan University, Taipei, Taiwan 106; Fax + 886 2 23 64 49 71; E-mail: tyluh@ccms.ntu.edu.tw
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Publication Date:
31 December 2001 (online)

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Reaction of allylic dithioacetals with organocuprate or organolithium reagent followed by treatment with a variety of alkyl electrophiles gives the corresponding E and Z isomeric mixture of vinyl sulfides in good yield. Further cross coupling with a Grignard reagent in the presence of NiCl2(dppe) affords the corresponding alkylation products in good yield. In general, the Grignard reagent having the same alkyl group as the R2 substituent in 1 is employed so that the stereochemical problem in coupling products can be lifted.

allylic dithioacetals - organocuprate - electrophiles - cross coupling - zwitterion synthon

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