Proline-catalyzed asymmetric addition reaction of 9-tosyl-3,4-dihydro-β-carboline with ketones

被引：145

作者：

Itoh, T ^{[1
]}

Yokoya, M ^{[1
]}

Miyauchi, K ^{[1
]}

Nagata, K ^{[1
]}

Ohsawa, A ^{[1
]}

机构：

[1] Showa Univ, Sch Pharmaceut Sci, Shinagawa Ku, Tokyo 1428555, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 23期

关键词：

D O I：

10.1021/ol030103x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

9-Tosyl-3,4-dihydro-beta-carboline (1) reacted with a ketone in the presence of (S)-proline as a catalyst to give the corresponding addition product in good yield and high enantioselectivity. In the process, a small amount of water was found to affect the stereoselectivity of the products. The system was applied to reaction of compound 1 and 3-buten-2-one to give 3,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-one, which is a versatile precursor for the synthesis of some indole alkaloids.

引用

页码：4301 / 4304

页数：4

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