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

✍ Scribed by Matthieu Léautey; Géraldine Castelot-Deliencourt; Philippe Jubault; Xavier Pannecoucke; Jean-Charles Quirion

Book ID: 104252407
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 164 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02250-5

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✦ Synopsis

Phosphine-borane can be diastereoselectively added to chiral a,b-unsaturated amides 3, using amino-alcohols as chiral inducers, leading to a-substituted b-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.

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