Synthesis of enantiopure mono- and disubstituted tetrahydroisoquinolines by 6-exo radical cyclizations

被引：18

作者：

Pedrosa, R ^{[1
]}

Andrés, C ^{[1
]}

Iglesias, JM ^{[1
]}

Obeso, MA ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 18期

关键词：

radical cyclizations; stereoselection; asymmetric synthesis; isoquinolines;

D O I：

10.1016/S0040-4020(01)00274-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(o-Bromophenyl)-3-allyl- and 2-allyl-3-(o-bromobenzyl)-substituted perhydrobenzoxazines, derived from (-)-8-amino menthol, readily cyclized stereoselectively by reaction with tributyltin hydride in the presence of AIBN. The cyclization compounds were transformed into enantiopure 4-alkyl tetrahydroisoquinolines by reductive ring opening of the N,O-acetal moiety with Lithium aluminum hydride. Enantiopure 1,4- and 3,4-dialkyl-substituted tetrahydroisoquinolines were also prepared by reaction of the cyclized compounds with methylmagnesium iodide and subsequent elimination of the menthol appendage. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4005 / 4014

页数：10

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