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Synthesis of α-Substituted β-Amidophosphines by Diastereoselective Alkylation. A New Access to Chiral Ligands for Asymmetric Catalysis

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

Book ID
120657788
Publisher
American Chemical Society
Year
2001
Tongue
English
Weight
73 KB
Volume
66
Category
Article
ISSN
0022-3263

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📜 SIMILAR VOLUMES

Alternative synthesis of α-substituted β
Alternative synthesis of α-substituted β-amidophosphines by [1,4]-addition. A new route to chiral ligands
✍ Matthieu Léautey; Géraldine Castelot-Deliencourt; Philippe Jubault; Xavier Panne 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 164 KB

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

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Diastereoselective synthesis of chiral non-racemic 2-substituted 2-boranatophosphino ethanoic acid: a potential intermediate to chiral ligands for asymmetric catalysis
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Chiral a-amidophosphine boranes 7a-b can be diastereoselectively alkylated, using a phenylglycinol derivative as a chiral inducer, to furnish a-substituted a-amidophosphine boranes 8-12 with up to 99% diastereoisomeric excess. Selective reduction of the amidophosphine boranes afforded optically pure