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The hetero Diels–Alder reaction featuring 2-phenyl-4-dimethylamino-1-thia-3-azabuta-1,3-diene as diene component: a clear example of a thermodynamically-controlled process

✍ Scribed by Gaëlle Trippé; Julien Perron; Anne Harrison-Marchand; Virginie Dupont; André Guingant; Jean-Paul Pradère; Loı̈c Toupet

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 93 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01203-0

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✦ Synopsis

Cycloaddition reactions of diene 1a with various dienophiles lead to trans 4,5-disubstituted dihydro-1,3-thiazine adducts. We demonstrate that a thermodynamically-controlled process, in which the adduct N-3 nitrogen plays a prominent role, accounts for the observed trans relative configuration.

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