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

✍ Scribed by Yoshiaki Takaya; Masamichi Ogasawara; Tamio Hayashi

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 84 KB
Volume: 12
Category: Article
ISSN: 0899-0042
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<469::aid-chir29>3.0.co;2-h

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✦ Synopsis

Reaction of 2-cyclohexenone with phenylboronic acid in the presence of 3 mol% 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-phenylcyclohexanone of up to 99% ee. The high enantioselectivity was achieved by 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.

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