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
收藏
页码：248 / 266
页数：19
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