Asymmetric 1,4-addition of phenylboronic acid to 2-cyclohexenone catalyzedby Rh(I)/binap complexes

Authors
Takaya, Y Ogasawara, M Hayashi, T
Citation
Y. Takaya et al., Asymmetric 1,4-addition of phenylboronic acid to 2-cyclohexenone catalyzedby Rh(I)/binap complexes, CHIRALITY, 12(5-6), 2000, pp. 469-471
Citations number
18
Categorie Soggetti
Chemistry & Analysis
Journal title
CHIRALITY
ISSN journal
08990042 → ACNP
Volume
12
Issue
5-6
Year of publication
2000
Pages
469 - 471
Database
ISI
SICI code
0899-0042(2000)12:5-6<469:A1OPAT>2.0.ZU;2-W
Abstract
Reaction of 2-cyclohexenone with phenylboronic acid in the presence of 3 mo l% of a rhodium(I)/(S)-binap catalyst in dioxane/H2O (10/1) at 100 degrees C proceeded with high enantioselectivity to give a high yield of (S)-3-phen ylcyclohexanone of up to 99% ee. The high enantioselectivity was achieved b y use of a catalyst generated in situ from Rh(acac)(C2H4)(2) and (S)-binap or Rh(acac)((S)-binap) as an isolated rhodium-phosphine complex. (C) 2000 W iley-Liss, Inc.