88726-08-3Relevant articles and documents
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
supporting information, 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.).
Regioselective and stereoselective sulfonylation of alkynylcarbonyl compounds in water
Li, Wenyi,Yin, Guoxing,Huang, Lei,Xiao, Yan,Fu, Zhimin,Xin, Xiu,Liu, Fang,Li, Zhizhang,He, Weimin
, p. 4879 - 4883 (2016/10/06)
With water as the reaction medium, an efficient protocol has been developed for the synthesis of Z-β-sulfonyl-α,β-unsaturated carbonyl products via water-promoted sulfonylation of alkynylcarbonyl compounds with sodium sulfinates. This strategy could effectively avoid the use of toxic organic solvents, catalysts and additives. This method features a wide substrate scope with a broad range of functional group tolerance, utilizes easily available starting materials, can be scaled-up, and is operationally simple.
Photochemical reactions of chromium-alkoxycarbene complexes with stabilized ylides to produce "push-pull" captodative allenes
Sestrick, Michael R.,Miller, Michael,Hegedus, Louis S.
, p. 4079 - 4088 (2007/10/02)
Photolysis of chromium alkoxycarbene complexes in the presence of stabilized ylides produced allenes having electron withdrawing groups on C-1 and electron donating groups on C-3. These highly reactive captodative allenes rearranged to 1,3-substituted-1,3-dienes under mildly acidic conditions and hydrolyzed to γ-keto-α,β-unsaturated esters, both in excellent yield.
