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Synthesis 2011(19): 3123-3132  
DOI: 10.1055/s-0030-1260187
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Induction by (S)-4-Isopropyl-1-phenylimidazolidin-2-thione in Titanium-Mediated Aldol Reactions and Its Application in Enantioselective Synthesis of (R)-Baclofen

Gopal L. Khatik, Ravi Khurana, Varun Kumar, Vipin A. Nair*
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector 67, Mohali, Punjab 160062, India
Fax: +91(172)2214692; e-Mail: vn74nr@yahoo.com; e-Mail: vnair@niper.ac.in ;
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Publication History

Received 25 May 2011
Publication Date:
24 August 2011 (online)

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Abstract

The usefulness of (S)-4-isopropyl-1-phenylimidazolidin-2-thione as a chiral auxiliary in stereoselective propionate and acetate aldol reactions is discussed. Further, the enantioselective synthesis of (R)-baclofen by acetate aldol reaction using the chiral auxiliary was demonstrated.

Key words

titanium - aldol reaction - asymmetric synthesis - chiral auxiliaries - stereoselectivity

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