260413-13-6Relevant academic research and scientific papers
On the mechanism and diastereoselectivity of 2,3-dihydrobenzofuran formation from sulfinylbenzoquinones and 2-trimethylsilyloxyfuran
Carreno, M. Carmen,Garcia Ruano, Jose L.,Urbano, Antonio,Remor, Cynthia Z.,Arroyo, Yolanda
, p. 4357 - 4367 (1999)
A mechanistic study of the reactions between 2-trimethylsilyloxyfuran 1 and (SS)-2-(arylsulfinyl)-1,4-benzoquinones 2a and 2b, giving rise to the diastereoselective formation of [3aS,8bS,SS]-3a,8b-dihydro-7-hydroxy-8- (arylsulfinyl)furo[3,2-b]benzofuran-2(3H)-ones 3a and 3b, is reported. The detection and 1H NMR characterization of several precursors of 3a and 3b accounts for a Michael-type initial reaction which dictates the final diastereoselection of the process. A significant improvement of the stereoselectivity (up to 96% de) in the formation of the tert-butylsulfinyl substituted derivative 3c was achieved by using 2-(tert-butylsulfinyl)-1,4- benzoquinone 2c as the starting quinone. (C) 1999 Elsevier Science Ltd.
