Stereocontrol of β-lactam formation using microwave irradiation

Formation of β-lactams by the reaction of an acid chloride, a Schiff base and a tertiary amine seems to involve multiple pathways some of which are very fast at higher temperatures. When β-lactam formation is conducted in open vessels in unmodified domestic microwave ovens, high level irradiation le...

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Bibliographic Details
Published inTetrahedron letters Vol. 36; no. 2; pp. 213 - 216
Main Authors Bose, Ajay K., Banik, Bimal K., Manhas, Maghar S.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.01.1995
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMISTRY
C-13 SIDE-CHAIN
ORGANIC-REACTION ENHANCEMENT
TAXOL
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Summary:Formation of β-lactams by the reaction of an acid chloride, a Schiff base and a tertiary amine seems to involve multiple pathways some of which are very fast at higher temperatures. When β-lactam formation is conducted in open vessels in unmodified domestic microwave ovens, high level irradiation leads to preferential formation of trans β-lactams in several cases when the Schiff base is derived from an aryl aldehyde rather than glyceraldehyde acetonide. High level irradiation of a mixture of a Schiff base, an acid chloride and a tertiary amine in a domestic microwave oven in open vessels leads to preferential formation of trans β-lactams in several case.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(94)02225-Z