An asymmetric substrate-controlled Morita-Baylis-Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines

被引：8

作者：

Luna-Freire, Kristerson R. ^{[1
]}

Scaramal, Joao Paulo S. ^{[1
]}

Resende, Jackson A. L. C. ^{[2
]}

Tormena, Claudio F. ^{[3
]}

Oliveira, Fabio L. ^{[4
]}

Aparicio, Ricardo ^{[4
]}

Coelho, Fernando ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Chem, Lab Synth Nat Prod & Drugs, BR-13083970 Campinas, SP, Brazil

[2] Inst Quim UFF, Xray Diffract Lab, Niteroi, RJ, Brazil

[3] Univ Estadual Campinas, Inst Chem, Lab Phys Organ Chem, BR-13083970 Campinas, SP, Brazil

[4] Univ Estadual Campinas, Inst Chem, Lab Struct Biol & Crystallog, BR-13083970 Campinas, SP, Brazil

来源：

TETRAHEDRON | 2014年 / 70卷 / 20期

基金：

巴西圣保罗研究基金会;

关键词：

Morita-Baylis-Hillman; Heterocycles; Pyrrolizidines; Heck reaction; Stereoselectivity; Absolute configuration; ELECTROSPRAY-IONIZATION MASS; STEREOSELECTIVE-SYNTHESIS; ALPHA-GLUCOSIDASE; NATURAL OCCURRENCE; BETA-GLUCOSIDASE; CYCLIC NITRONES; AB-INITIO; INHIBITORS; CYCLOADDITION; IMINOSUGARS;

D O I：

10.1016/j.tet.2013.10.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：3319 / 3326

页数：8

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