Synthesis 2003(9): 1441-1445
DOI: 10.1055/s-2003-40189
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective 1,3-Dipolar Cycloaddition of Ynolates with Chiral Nitrones

Mitsuru Shindo*a,b, Kotaro Itohb, Keiko Ohtsukia, Chinatsu Tsuchiyaa, Kozo Shishidoa
a Institute for Medicinal Resources, University of Tokushima, Sho-machi 1, Tokushima 770-8505, Japan
Fax: +81(88)6337294; e-Mail: shindo@ph2.tokushima-u.ac.jp;
b PRESTO, Japan Science and Technology Corporation (JST)
Further Information

Publication History

Received 28 April 2003
Publication Date:
24 June 2003 (online)

Abstract

Asymmetric inverse electron-demand 1,3-dipolar cycloaddition of ynolates with chiral nitrones produced 5-isoxazoli­dinones with good diastereoselectivity. These products were easily converted into optically pure β-amino acids and chiral γ-butyrolactones.