Synthesis of enantiopure highly functionalized pyrrolizines and indolizines from natural α-amino acids:: An experimental and theoretical investigation

被引：27

作者：

Borsini, Elena ^{[1
]}

Broggini, Gianluigi ^{[1
,2
]}

Contini, Alessandro ^{[2
,3
]}

Zecchi, Gaetano ^{[1
,2
]}

机构：

[1] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

[2] Ctr Interuniv Ric Reaz Pericicl & Sintesi Sistemi, I-20133 Milan, Italy

[3] Univ Milan, Ist Chim Org A Marchesini, Fac Farm, I-20133 Milan, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 16期

关键词：

cycloaddition; nitrones; regioselectivity; density functional calculations; pi interactions;

D O I：

10.1002/ejoc.200701217

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Variously substituted enantiopure 2-benzylamino-1-hydroxymethyl-2,3-dihydro-1H-pyrrolizines and 6-benzyl-amino-5,6,7,8-tetrahydroindolizin-8-ols have been prepared. The reaction sequence starts from L-a-amino acids and involves an intramolecular cycloaddition of pyrrole-based nitrone intermediates. A theoretical investigation at the HCTH/6-311+G(d,p)//HCTH/6-31+G(d) level of theory was performed with the aim of rationalizing the effects of substituents on the regiochemistry of the cycloaddition reaction. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：2808 / 2816

页数：9

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