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Microwave‐Assisted Organocatalytic Enantioselective Intramolecular aza‐Michael Reaction with α,β‐Unsaturated Ketones
Author(s) -
Fustero Santos,
del Pozo Carlos,
Mulet Cristina,
Lazaro Rubén,
SánchezRoselló María
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101292
Subject(s) - enantioselective synthesis , intramolecular force , michael reaction , chemistry , catalysis , enantiomer , organocatalysis , microwave irradiation , conjugated system , organic chemistry , combinatorial chemistry , polymer
An organocatalytic enantioselective intramolecular aza‐Michael reaction of carbamates bearing conjugated ketones as Michael acceptors is described. By using 9‐amino‐9‐deoxy‐ epi ‐hydroquinine as the catalyst and pentafluoropropionic acid as a co‐catalyst, a series of piperidines, pyrrolidines, and the corresponding benzo‐fused derivatives (indolines, isoindolines, tetrahydroquinolines, and tetrahydroisoquinolines) can be obtained in excellent yields and enantioselectivities. In addition, the use of microwave irradiation at 60 °C improves the efficiency of the process giving rise to the final products with comparable yields and enantiomeric excesses. Some mechanistic insights are also considered.