10138-60-0Relevant articles and documents
Stereoselective synthesis of β-ketoesters from prop-2-yn-1-ols
Darcel, Christophe,Bruneau, Christian,Dixneuf, Pierre H.,Roberts, Stanley M.
, p. 9241 - 9252 (1997)
The activation of allylic prop-2-yn-1-ols by the [Ru(μ-O2CH)(CO)2(PPh3)]2 catalyst in the presence of carboxylic acids leads to unsaturated β-ketoesters in one step. The utilization of optically active prop-2-yn-1-ols provides a new stereoselective access to optically active β-ketoesters with retention of configuration at the propargylic carbon.
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Kenyon,Poplett
, p. 274 (1945)
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Shackelford et al.
, p. 1631 (1962)
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Hennion,Lieb
, p. 1289 (1944)
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Rhodium-catalyzed synthesis of 1,2-dihydropyridine by a tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole
Dai, Haican,Yu, Sisi,Cheng, Wanli,Xu, Ze-Feng,Li, Chuan-Ying
supporting information, p. 6417 - 6420 (2017/07/10)
A tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole including formation of α-imino rhodium carbene, 1,2-migration of an acetoxy group and six electron electrocyclic ring closure was reported. The migration of the OAc group with excellent chemoselectivity was the crucial process, leading to the formation of 1,2-dihydropyridine specifically in up to 90% yield. Several transformations of the dihydropyridine product were also achieved illustrating the potential of the protocol in organic synthesis. Based on the observation of the intermediate, a plausible mechanism was proposed.
Simultaneous synthesis of both rings of chromenes via a benzannulation/ o -quinone methide formation/electrocyclization cascade
Majumdar, Nilanjana,Korthals, Keith A.,Wulff, William D.
supporting information; experimental part, p. 1357 - 1362 (2012/03/11)
A new route to the chromene ring system has been developed which involves the reaction of an α,β-unsaturated Fischer carbene complex of chromium with a propargyl ether bearing an alkenyl group on the propargylic carbon. This transformation involves a cascade of reactions that begins with a benzannulation reaction and is followed by the formation of an o-quinone methide, and finally results in the emergence of a chromene upon an electrocyclization. This reaction was extended to provide access by employing an aryl carbene complex. This constitutes the first synthesis of chromenes in which both rings of the chromene system are generated in a single step and is highlighted in the synthesis of lapachenole and vitamin E.
