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Diastereoselective Synthesis of Amino‐Substituted Indolizidines and Quinolizidines by the Intramolecular Hetero‐Ene Reaction of Prolinal Imine and 2‐Piperidine Carbaldimine
Author(s) -
Laschat Sabine,
Grehl Matthias
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199404581
Subject(s) - piperidine , chemistry , isopropyl , imine , ene reaction , lewis acids and bases , intramolecular force , stereochemistry , organic chemistry , catalysis
The choice of Lewis acid determines the stereochemistry and structure of the products in the cyclization of 1 . Whereas with FeCl 3 the benzylamino(isopropenyl) compounds 2 are formed preferably, in the presence of TiCl 4 the main products are benzylideneamino(isopropyl)‐substituted compounds 3 .
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