1907-69-3Relevant articles and documents
Preparation method of alpha,beta-unsaturated carbonyl compound with high stereoselectivity and beta-sulfonylation
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Paragraph 0021; 0056, (2019/01/05)
The invention discloses a preparation method of an alpha,beta-unsaturated carbonyl compound with high stereoselectivity and beta-sulfonylation. Alkyne without electrons and a sulfonyl source are subjected to a hydrogenation sulfonylation reaction to obtai
Regio- and Stereoselective Hydrosulfonylation of Electron-Deficient Alkynes: Access to Both E- and Z-β-Sulfonyl-α,β-Unsaturated Carbonyl Compounds
Zhang, Wei,Johnson, Gabriel M.,Guan, Zhi,He, Yan-Hong
, p. 4562 - 4570 (2018/10/24)
A metal-free hydrosulfonylation of electron-deficient alkynes with sodium sulfinates or sulfinic acids to access both E- and Z-β-sulfonyl-α,β-unsaturated carbonyl compounds has been developed. We propose that this reaction via a hydroxylallene intermediate delivers the thermodynamically stable E isomer, or via a concerted termolecular AdE3 mechanism affords Z isomer. The stereoselectivity of addition (syn or anti) can be controlled by varying the sulfonyl sources and acidic buffer solutions. This protocol exhibits broad substrate scope for internal or terminal alkynes including various substituted ynones and alkynyl esters. This approach is mild, efficient, operationally simple and easy to be scaled-up. (Figure presented.).
