Synthèse stéréosélective des sulfones vinyliques Z et E.

作者: Marc Julia , Michèle Launay , Jean-Pierre Stacino , Jean-Noël Verpeaux

DOI: 10.1016/S0040-4039(00)87369-4

关键词:

摘要: Abstract The condensation of α-sulphonyl carbanions with esters or aldehydes (followed in this case by oxidation) gives β-ketosulphones. These were reduced stereoselectively into threo β-hydroxysulphones. Basic conditions have been found where the corresponding tosylates are converted Z vinylic sulphones whereas erythro lead to E isomer. acetoxy-sulphones threo, under different alkaline same sulphone a “convergent” manner.

参考文章(6)
Herbert O. House, Rolland S. Ro, The Stereochemistry of Elimination Reactions Involving Halohydrin Derivatives and Metals1 Journal of the American Chemical Society. ,vol. 80, pp. 182- 187 ,(1958) , 10.1021/JA01534A046
Philip J. Kocienski, Basil Lythgoe, Steven Ruston, Scope and stereochemistry of an olefin synthesis from β-hydroxysulphones J. Chem. Soc., Perkin Trans. 1. ,vol. 9, pp. 829- 834 ,(1978) , 10.1039/P19780000829
Philip J. Kocienski, Basil Lythgoe, Ian Waterhouse, The influence of chain-branching on the steric outcome of some olefin-forming reactions Journal of the Chemical Society, Perkin Transactions 1. ,vol. 11, pp. 1045- 1050 ,(1980) , 10.1039/P19800001045
Charles J. M. Stirling, Leaving groups and nucleofugality in elimination and other organic reactions ChemInform. ,vol. 10, pp. 198- 203 ,(1979) , 10.1021/AR50138A002