4720-68-7Relevant articles and documents
Formal Asymmetric Catalytic Thiolation with a Bifunctional Catalyst at a Water-Oil Interface: Synthesis of Benzyl Thiols
Guo, Wengang,Wu, Bo,Zhou, Xin,Chen, Ping,Wang, Xu,Zhou, Yong-Gui,Liu, Yan,Li, Can
, p. 4522 - 4526 (2015)
The enantioselective conjugated addition of tritylthiol to in situ generated ortho-quinone methides (o-QMs) is catalyzed by an acid-base bifunctional squaramide organocatalyst. The transformation proceeds with high yield (up to 99%) and stereoselectivity (up to 97:3 e.r.) using water as solvent under mild conditions. The catalyst system provides a new strategy for the synthesis of optically active benzyl mercaptans. Control experiments suggested that o-QMs are generated by the tertiary amine moiety of the squaramide organocatalyst and that the water-oil biphase is crucial for achieving high reactivity and stereoselectivity.
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Fukui,Nakayama
, p. 1321 (1962)
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Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles
Huang, You,Li, Xiaohu
supporting information, p. 9934 - 9937 (2021/10/12)
A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.
An unexpected Pummerer rearrangement in the synthetic route to ethyl (2′-hydroxy-4′,5′-methylenedioxyphenyl)acetate: An alternative approach to 2,3-dimethylthio benzofurans
Carre?o-Montero, Ariel,Maldonado, Luis A.,Chávez, María Isabel,Hernández-Ortega, Simón,Delgado, Guillermo
, (2019/11/03)
The synthesis of ethyl (2′-hydroxy-4′,5′-methylendioxophenyl)acetate, a fragment of the antihyperglycemic natural coumarin subcoriacin, is reported. We found an expeditious route to the title compound in five steps. Final metal catalyzed acid ethanolysis of the vinylic 1,1-methylthio methylsulfoxide derivative afforded the required aryl acetic ester, but in the absence of metal catalyst, an unexpected Pummerer rearrangement produced the 2,3-dimethylthiofuran derivative as the major product. This last result provides an alternative entry to 2,3-dimethlythiobenzofurans.