INDIUM MEDIATED ALLYLATION OF N-tert-BUTANESULFINYL IMINES WITH 1,3-DIBROMOPROPENE: STEREOSELECTIVE SYNTHESIS OF AZIRIDINES

被引：6

作者：

Macia, Edgar ^{[1
,2
,3
]}

Foubelo, Francisco ^{[1
,2
,3
]}

Yus, Miguel ^{[1
,3
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Apdo 99, E-03080 Alicante, Spain

[2] Univ Alicante, Inst Sintesis Organ, Apdo 99, E-03080 Alicante, Spain

[3] Univ Alicante, Ctr Innovac Quim Avanzada ORFEO CINQA, Apdo 99, E-03080 Alicante, Spain

来源：

HETEROCYCLES | 2019年 / 99卷 / 01期

关键词：

ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE ALLYLATION; CONVENIENT SYNTHESIS; HENRY REACTION; ALDEHYDES; DERIVATIVES; TETRAHYDROQUINOLINE; ADDITIONS; REDUCTION;

D O I：

10.3987/COM-18-S(F)18

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of N-tert-butanesulfinyl imines 1 with 1,3-dibromopropene (2), in the presence of indium metal, in saturated aqueous solution of sodium bromide, produced bromohomoallylamine derivatives 3 with total facial diastereoselectivity for the imine addition, and moderate yields. These compounds were easily transformed into the corresponding vinyl aziridines 5 upon deprotonation with KHMDS in THF, the intramolecular cyclization taking place in a stereospecific manner in moderate to high yields.

引用

页码：248 / 266

页数：19

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