ASYMMETRIC-SYNTHESIS OF 3-HYDROXYPROLINES BY PHOTOCYCLIZATION OF N-(2-BENZOYLETHYL)GLYCINAMIDES

被引：37

作者：

WESSIG, P ^{[1
]}

WETTSTEIN, P ^{[1
]}

GIESE, B ^{[1
]}

NEUBURGER, M ^{[1
]}

ZEHNDER, M ^{[1
]}

机构：

[1] UNIV BASEL,DEPT CHEM,CH-4056 BASEL,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1994年 / 77卷 / 03期

关键词：

D O I：

10.1002/hlca.19940770322

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The chiral N-(2-benzoylethyl)-N-tosylglycinamides 1a-e were prepared from the C-2-symmetric pyrrolidines 5a-c. Irradiation of these ketones 1a-e gave cis-3-hydroxyprolinamides 10-12 in moderate to good yields (Scheme 3). The de of the photocyclizations depended on the size of the substituents in positions C(2) and C(5) of the chiral pyrrolidine auxiliaries. In addition, the de varied with the reaction temperature, allowing the determination of activation-parameter differences. The structure of products 10-12 were established by NMR and X-ray analyses.

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页码：829 / 837

页数：9

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