Tetrahedron p. 3919 - 3930 (1988)
Update date:2022-07-30
Topics:
Daub, G. William
Heerding, Dirk A.
Overman, Larry E.
Trans-2,6-disubstituted-1,2,5,6-tetrahydropyridines are formed stereoselectively from the cyclization of silicon-containing iminium cations 5 if the nitrogen substituents R1 is an alkyl group.In contrast, cyclization of the corresponding NH or N-acyl iminium ions occurs in a stereorandom fashion.Nonracemic tetrahydropyridines cannot be prepared in this way, since both iminium ion and N-acyliminium ion intermediates racemize prior to cyclization.
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(1988)
