Enantioselective construction of quaternary alpha-carbon centers on alpha-amino phosphonates via catalytic asymmetric allylation

Authors
Kuwano, R Nishio, R Ito, Y
Citation
R. Kuwano et al., Enantioselective construction of quaternary alpha-carbon centers on alpha-amino phosphonates via catalytic asymmetric allylation, ORG LETT, 1(6), 1999, pp. 837-839
Citations number
44
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
6
Year of publication
1999
Pages
837 - 839
Database
ISI
SICI code
1523-7060(19990923)1:6<837:ECOQAC>2.0.ZU;2-1
Abstract
[GRAPHICS] Asymmetric allylation of alpha-acetamido beta-keto phosphonates was promote d, in the presence of potassium tert-butoxide as a base, by a palladium cat alyst prepared from [Pd(pi-allyl)(cod)]BF4 and (R)-BINAP and gave the corre sponding alpha-alkyl alpha-amino phosphonic acid derivatives with 65-88% ee . Diastereoselective reduction of the carbonyl group in the product was acc omplished by NaBH4 or BU4NBH4. The diastereoselection in the reduction was reversed by choice of solvent.