Premium
N , N ‐Dialkylhydrazones as the Imine Component in the Staudinger‐Like [2+2] Cycloaddition to Benzyloxyketene
Author(s) -
Fernández Rosario,
Ferrete Ana,
Lassaletta José M.,
Llera José M.,
MartínZamora Eloísa
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020301)41:5<831::aid-anie831>3.0.co;2-6
Subject(s) - imine , cycloaddition , toluene , aldehyde , chemistry , staudinger reaction , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis
To overcome the limitations of using unstable imines in Staudinger cycloadditions to ketenes, aldehyde N , N ‐dialkylhydrazones 1 were used as stable imines. This strategy and a fine tuning of the auxiliary result in a straightforward synthesis of cycloadducts 2 , deprotected β ‐lactams 3 , and isoserines 4 (see scheme: a) Et 3 N, toluene, ▵; b) 1. magnesium monoperoxyphthalate, 2. H 2 , Pd/C; c) H + ).