STEREOSELECTIVE RADICAL ADDITIONS USING CHIRAL 1,3-DIOXOLANONES DERIVED FROM LACTIC AND MALIC-ACID

被引：7
|
作者：
KNEER, G
MATTAY, J
HEIDBREDER, A
RAABE, G
KREBS, B
LAGE, M
机构：
[1] UNIV MUNSTER,INST ORGAN CHEM,D-48149 MUNSTER,GERMANY
[2] RHEIN WESTFAL TH AACHEN,INST ORGAN CHEM,W-5100 AACHEN,GERMANY
[3] UNIV MUNSTER,INST ANORGAN CHEM,W-4400 MUNSTER,GERMANY
来源：
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1995年 / 337卷 / 02期
关键词：
D O I：
10.1002/prac.19953370126
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The hydrogen abstraction of radical intermediates yielded by radical addition to the methylene compound 6, shows excellent facial selectivity. Conformational analyses of the radical intermediates were carried out by quantum chemical calculations and explain these results. The chiral radicals 7 and 8, yielded from the chiral bromides 3 and 4, lead with ethyl acrylate to the adducts 28 and 29 with more 96 % de. The adduct 28 was converted to the optically active gamma-valerolactone 30. The structures of the bromides 3, 4 and 31 as well as the radical adducts 19a, 24 and 25 have been verified by X-ray diffraction analysis.
引用
收藏
页码：113 / 124
页数：12
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