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High degree of exo selectivity in imino Diels-Alder reactions catalyzed by tert-butyldimethylsilyltriflate

✍ Scribed by Denise Nogue; Renée Paugam; Lya Wartski

Book ID: 104224665
Publisher: Elsevier Science
Year: 1992
Tongue: French
Weight: 245 KB
Volume: 33
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)91597-1

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✦ Synopsis

Diels-Alder reacfions ofsilyloxydiene 1 derivedfrom 1 -acetylcyclohexene with imincs 26 and 2c occur with high exe selectivity depending upon experimental cundirinns: exo cycloadducts 3h-c are e_zciusively formed under kinetic control using rerf-butyIdimethyt.rilyllriflate us catalyst. In [he presence of ~lC13, lender thermodynamic control, high endu selectivity is only observed with 2b. Lewis acids catalyzed imirlo Dlels~Aldcr processes play an important role in heterocyclic s> nthesis. Xevertheless, their potentiality strongly relies upon their stereocontrol (1,2). We have previously reporred that the stereoselectivity of the reaction of trimethylsilylenolether of I-acetylcyclohexenc 1 and henzylideneaniline 2a under Lewis acid catalysis strongly depended upon experimental conditions. Thus in the presence of AlC13, under kinetic conditions, the exe adduct 3a was favnured (3a/4a = 84/lhl while under thermodynamic control. the endo adduct 4a was mainly formed (3a/la = 5'95; ruble I. entries 1 7)(L). .-Ch(CH,), i ch(CH2)3 bSi(CK& 0 1 2 3 exe 4 endo 5

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