Alternative synthesis of α-substituted β-amidophosphines by [1,4]-addition. A new route to chiral ligands

Phosphine–borane can be diastereoselectively added to chiral α,β-unsaturated amides 3 , using amino-alcohols as chiral inducers, leading to α-substituted β-amidophosphine boranes 4 with up to 74% diastereomeric excess. Selective deprotection afforded optically pure carboxylic derivatives 5 which are...

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Bibliographic Details
Published inTetrahedron letters Vol. 43; no. 50; pp. 9237 - 9240
Main Authors Léautey, Matthieu, Castelot-Deliencourt, Géraldine, Jubault, Philippe, Pannecoucke, Xavier, Quirion, Jean-Charles
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.12.2002
Elsevier
Subjects
asymmetric catalysis
Chemistry
Chemistry, Organic
chiral ligands
diastereoselective Michael addition
Physical Sciences
Science & Technology
diastereoselective Michael addition
chiral ligands
asymmetric catalysis
CATALYSIS
ASYMMETRIC-SYNTHESIS
ACID
DIASTEREOSELECTIVE SYNTHESIS
COMPLEXES
GRIGNARD-REAGENTS
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Summary:Phosphine–borane can be diastereoselectively added to chiral α,β-unsaturated amides 3 , using amino-alcohols as chiral inducers, leading to α-substituted β-amidophosphine boranes 4 with up to 74% diastereomeric excess. Selective deprotection afforded optically pure carboxylic derivatives 5 which are key intermediates for the synthesis of various potential chiral ligands for asymmetric catalysis. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)02250-5