A chiral 1,4-oxazin-2-one:: asymmetric synthesis versus resolution, structure, conformation and VCD absolute configuration

被引：24

作者：

Solladié-Cavallo, A ^{[1
]}

Sedy, O

Salisova, M

Biba, M

Welch, CJ

Nafié, L

Freedman, T

机构：

[1] Univ Strasbourg 1, ECPM, F-67087 Strasbourg, France

[2] Comenius Univ, Dept Organ Chem, Bratislava 84215, Slovakia

[3] Merck & Co Inc, Rahway, NJ 07065 USA

[4] Syracuse Univ, Dept Chem, Syracuse, NY 13244 USA

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 19期

关键词：

D O I：

10.1016/S0957-4166(01)00478-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

1,4-Oxazin-2-one 3 is obtained from 2-pinanone in 4 steps and 78% overall yield. Enantiopure (e.e. > 99%) (R)-(+)-3 and (S)-(-)-3 were obtained through chiral supercritical fluid chromatography (using a semi preparative Chiralpak AS column) with almost quantitative recovery of material. The structure and the boat-conformation of the lactone ring have been determined by NMR and the absolute configuration determined by VCD. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2703 / 2707

页数：5

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