A new polymer-supported Evans-type chiral auxiliary derived from α-hydroxy-β-amino acid, phenylnorstatine:: synthesis and application in solid-phase asymmetric alkylation reactions

被引：27

作者：

Kotake, T ^{[1
]}

Rajesh, S ^{[1
]}

Hayashi, Y ^{[1
]}

Mukai, Y ^{[1
]}

Ueda, M ^{[1
]}

Kimura, T ^{[1
]}

Kiso, Y ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Dept Med Chem, Ctr Frontier Res Med Sci, Yamashima Ku, Kyoto 6078412, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 18期

关键词：

Evans' oxazolidinone; chiral auxiliary; phenylnorstatine; asymmetric alkylation; solid-phase; polymer-supported;

D O I：

10.1016/j.tetlet.2004.03.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Based on a new anchoring strategy, a polymer-supported chiral oxazolidinone was prepared starting from (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid (phenylnorstatine, Pns) and Wang resin. Solid-phase asymmetric alkylation on this resin proceeded in high diastereoselectivity comparable to that of conventional solution-phase model experiments. This study suggests that anchoring through the 5-position of oxazolidinone is highly suited to achieving diastereoselective alkylation reactions on solid-support. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3651 / 3654

页数：4

共 23 条

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[Anonymous], [No title captured]

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