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Selective Transformations of β‐Keto Esters, Promoted by Dowex Basic Ion‐Exchange Resins
Author(s) -
Simon Céline,
Peyronel JeanFrançois,
Clerc François,
Rodriguez Jean
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200210)2002:19<3359::aid-ejoc3359>3.0.co;2-7
Subject(s) - chemistry , intramolecular force , michael reaction , adduct , ion exchange resin , bicyclic molecule , ion exchange , organic chemistry , ion , medicinal chemistry , catalysis
Depending on the nature of the Dowex basic ion‐exchange resin, cyclic β‐keto esters 1 react with α,β‐unsaturated aldehydes 2 to give either the corresponding Michael adducts 3 or the highly functionalized bicyclo[3.3.1]nonanes 4 in a one‐pot Michael addition−intramolecular aldolization sequence. Some selective transformations of the highly functionalized systems 3 and 4 to provide amino azabicyclo[3.3.1]nonanones 9 , polycyclic aminals 10 , and azacyclooctene 12 are also presented. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)