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

Mitsuru Shindo; Kotaro Itoh; Keiko Ohtsuki; Chinatsu Tsuchiya; Kozo Shishido

doi:10.1055/s-2003-40189

SPECIALTOPIC

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

Mitsuru Shindo*^a,b, Kotaro Itoh^b, Keiko Ohtsuki^a, Chinatsu Tsuchiya^a, Kozo Shishido^a
^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)

Abstract

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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.

Key words

asymmetric synthesis - cycloadditions - diastereoselectivity - nitrones - ynolates

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References

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