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Asymmetric 1,4‐addition of phenylboronic acid to 2‐cyclohexenone catalyzed by Rh(I)/binap complexes
Author(s) -
Takaya Yoshiaki,
Ogasawara Masamichi,
Hayashi Tamio
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:5/6<469::aid-chir29>3.0.co;2-h
Subject(s) - chemistry , phenylboronic acid , binap , rhodium , catalysis , cyclohexenone , phosphine , yield (engineering) , medicinal chemistry , enantioselective synthesis , organic chemistry , polymer chemistry , materials science , metallurgy
Reaction of 2‐cyclohexenone with phenylboronic acid in the presence of 3 mol% of a rhodium(I)/( S )‐binap catalyst in dioxane/H 2 O (10/1) at 100°C proceeded with high enantioselectivity to give a high yield of ( S )‐3‐phenylcyclohexanone of up to 99% ee. The high enantioselectivity was achieved by use of a catalyst generated in situ from Rh(acac)(C 2 H 4 ) 2 and ( S )‐binap or Rh(acac)(( S )‐binap) as an isolated rhodium‐phosphine complex. Chirality 12:469–471, 2000. © 2000 Wiley‐Liss, Inc.