Efficient syntheses and ring-opening reactions of trans- and cis-oxazoline-5-carboxylates

被引：39

作者：

Lee, SH

Yoon, J ^{[1
]}

Nakamura, K

Lee, YS

机构：

[1] Silla Univ, Dept New Mat Chem, Pusan 617736, South Korea

[2] Seoul Natl Univ, Sch Chem Engn, Seoul 151742, South Korea

[3] Inst Med Mol Design, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 09期

关键词：

D O I：

10.1021/ol005681h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

cis and trans-Oxazoline-5-carboxylates were synthesized efficiently from isopropyl trans-cinnamate utilizing the Sharpless AA reaction. trans-Oxazoline was much more reactive than the cis-isomer toward ring opening reactions. From ab initio molecular calculations, the cis-isomer was predicted to be less reactive than the trans-isomer by 2.7 kcal/mol. Both syn and anti acetylthio esters and anti diamino esters were synthesized from these cis- and trans-oxazoline-5-carboxylates.

引用

页码：1243 / 1246

页数：4

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