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Regiochemical control in asymmetric Diels-Alder cycloadditions of enantiopure (S)S-(p-tolylsulfinyl)-1,4-benzoquinones with Dane's diene

✍ Scribed by M.Carmen Carreño; JoséL García Ruano; Cynthia Z Remor; Antonio Urbano; Jean Fischer

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 243 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10439-7

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✦ Synopsis

Enantiopure sulfinylquinones (+)-2 and (+)-3 reacted with Dane's diene 1 under thermal and ZnBr 2 Lewis acid conditions with reversal regiochemistry but similar ~-facial diastereoselectivity to afford, after spontaneous elimination of the sulfinyl group, tetracyclic derivatives 4-9.

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