Enantioselective copper-catalyzed conjugate addition of diethylzinc to enones using new chiral P,N ligands composed of (S)-2-alkyl-2-aminoethylphosphines and alpha-substituted pyridines

Authors
Morimoto, T Yamaguchi, Y Suzuki, M Saitoh, A
Citation
T. Morimoto et al., Enantioselective copper-catalyzed conjugate addition of diethylzinc to enones using new chiral P,N ligands composed of (S)-2-alkyl-2-aminoethylphosphines and alpha-substituted pyridines, TETRAHEDR L, 41(51), 2000, pp. 10025-10029
Citations number
35
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
51
Year of publication
2000
Pages
10025 - 10029
Database
ISI
SICI code
0040-4039(200012)41:51<10025:ECCAOD>2.0.ZU;2-3
Abstract
New P,N ligands prepared from (S)-2-alkyl-2-aminoethylphosphines and alpha -substituted pyridines are efficient chiral ligands for the copper-catalyze d conjugate addition of diethylzinc to 2-cyclohexen-1-one and chalcone. The best result (90-91% ee) for the cyclohexenone was obtained with Cu(OTf)(2) (0.7-1 mol%) and a P,N ligand 4 derived from (S)-1-(diphenylphosphino)-3-m ethyl-2-butanamine and 6-methylpyridine-2-carboxaldehyde. (C) 2000 Elsevier Science Ltd. All rights reserved.