Chiral lithium amides on polymer support — Synthesis and use in deprotonation of ketones

A number of chiral secondary amines attached to Merrifield resin or to noncrosslinked (soluble) polystyrene support were synthesized. The corresponding lithium amides, generated from these amines by treatment with BuLi, react with tropinone, a model symmetrical ketone, to give the corresponding enol...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 84; no. 2; pp. 257 - 268
Main Authors Majewski, Marek, Ulaczyk-Lesanko, Agnieszka, Wang, Fan
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.02.2006
Natl Research Council Canada
Subjects
Amides
Amines
Chemical properties
Chemistry
Chemistry, Multidisciplinary
Chirality
Physical Sciences
Science & Technology
Canada
ORGANIC-SYNTHESIS
chiral lithium amides
ASYMMETRIC-SYNTHESIS
ACID
ENOLATE
enolates
INTERNAL PROTON RETURN
polymer-supported reagents
STEREOSELECTIVE SYNTHESIS
TROPANE ALKALOIDS
CYCLIC-KETONES
tropinone
CHEMISTRY
CATALYTIC ENANTIOSELECTIVE REARRANGEMENT
deprotonation
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Summary:A number of chiral secondary amines attached to Merrifield resin or to noncrosslinked (soluble) polystyrene support were synthesized. The corresponding lithium amides, generated from these amines by treatment with BuLi, react with tropinone, a model symmetrical ketone, to give the corresponding enolates enantioselectively (ee up to 75%). The enolates were trapped either as the corresponding aldol adducts by a reaction with benzaldehyde or as ring-opening products in a reaction with a chloroformate.Key words: chiral lithium amides, polymer-supported reagents, deprotonation, enolates, tropinone.
ISSN:0008-4042
1480-3291
DOI:10.1139/v06-006