Remarkable Electronic Effect on the Diastereoselectivity of the Heck Reaction of Methyl Cinnamate with Arenediazonium Salts: Formal Total Synthesis of (+/-)-Indatraline and (+/-)-Sertraline

Pastre, Julio Cezar; Duarte Correia, Carlos Roque

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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Remarkable Electronic Effect on the Diastereoselectivity of the Heck Reaction of Methyl Cinnamate with Arenediazonium Salts: Formal Total Synthesis of (+/-)-Indatraline and (+/-)-Sertraline

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Author(s):	Pastre, Julio Cezar ^[1] ; Duarte Correia, Carlos Roque ^[1] Total Authors: 2
Affiliation:	^[1] Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13083970 Campinas, SP - Brazil Total Affiliations: 1
Document type:	Journal article
Source:	ADVANCED SYNTHESIS & CATALYSIS; v. 351, n. 9, p. 1217-1223, JUN 2009.
Web of Science Citations:	51
Abstract
An efficient and stereoselective protocol for the preparation of beta,beta-disubstituted acrylates in good to high yields by means of a Heck-Matsuda arylation was accomplished. The method employs a base- and ligand-free Heck arylation reaction of methyl cinnamate using both electron-deficient and electron-rich arenediazonium salts as electrophiles. The Heck reaction displays a remarkable electronic dependence regarding the diastereoselectivity of the arylation process, which correlates with the electronic nature of the arenediazonium salts employed. A rationale for the observed diastereoselectivity is presented. The overall methodology provides a convenient route to 3-arylindanones and 4-aryltetralones allowing the concise formal total syntheses of the therapeutically important psychoactive compounds (+/-)-indatraline and (+/-)-sertraline. (AU)

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