Intermolecular antiselective and enantioselective reductive coupling of enones and aromatic aldehydes with chiral Rh(Phebox) catalysts

Takushi Shiomi; Takahiro Adachi; Jun-ichi Ito; Hisao Nishiyama

doi:10.1021/ol802939u

Intermolecular antiselective and enantioselective reductive coupling of enones and aromatic aldehydes with chiral Rh(Phebox) catalysts

Org Lett. 2009 Feb 19;11(4):1011-4. doi: 10.1021/ol802939u.

Authors

Takushi Shiomi¹, Takahiro Adachi, Jun-ichi Ito, Hisao Nishiyama

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan.

PMID: 19161317
DOI: 10.1021/ol802939u

Abstract

The intermolecular reductive coupling reaction of cyclopent-2-enone and aromatic aldehydes was realized by chiral rhodium-(bisoxazolinyl)phenyl catalysts, Rh(Phebox-Ph)(OAc)(2)(H(2)O), with diphenymethylsilane as a hydride donor to give the corresponding beta-hydroxyketones in high anti-selectivity (up to 96%) with high enantioselectivity (up to 93%).