The use of (-)-8-phenylisoneomenthol and (-)-8-phenylmenthol in the enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]heptane derivatives via aza-Diels-Alder reaction

被引：25
作者：
Cardoso do Vale, Maria Luisa
Rodriguez-Borges, Jos Enrique
Caamano, Olga
Fernandez, Franco
Garcia-Mera, Xerardo
机构：
[1] Univ Porto, Fac Ciencias, CIQ Dept Quim, P-4169007 Oporto, Portugal
[2] Univ Santiago de Compostela, Fac Farm, Dept Quim Organ, E-15782 Santiago De Compostela, Spain
来源：
TETRAHEDRON | 2006年 / 62卷 / 40期
关键词：
asymmetric synthesis; aza-Diels-Alder reaction; induction; chiral alcohols; ALPHA-AMINO-ACIDS; CARBOCYCLIC NUCLEOSIDES; CONVENIENT SYNTHESIS; EFFICIENT; 2-AZABICYCLO<2.2.1>HEPT-5-EN-3-ONE; CYCLOPENTADIENE; 8-PHENYLMENTHOL; STEREOISOMERS; GLYOXYLATES; RESOLUTION;
D O I：
10.1016/j.tet.2006.06.118
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The asymmetric aza-Diels-Alder reaction of the (1R)-8-phenylmenthyl or (1R)-8-phenylisoneomenthyl glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding pure [(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylates (80 or 69% yield, respectively). Reduction of these cycloadducts with LiAlH4 afforded pure (-)-[(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl] methanol. Furthermore, a reaction sequence based on Barbier-Wieland degradation of both (1S,3-exo)-adducts afforded pure (+)-(1R)-2-benzoyl-2-azabicyclo[2.2.1]heptan-3-one. In the course of the two transformation sequences referred, the chiral auxiliaries were recovered in a virtually quantitative way. (c) 2006 Elsevier Ltd. All rights reserved.
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页码：9475 / 9482
页数：8
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