Regio- and stereoselective Heck arylations of N-carbomethoxy-L-3-dehydroproline methyl ester with arenediazonium salts.: Total synthesis of neuroexcitatory aryl kainoids

被引：30

作者：

da Silva, Kezia Peixoto ^{[1
]}

Godoi, Marla Narciso ^{[1
]}

Duarte Correia, Carlos Roque ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, UNICAMP, BR-13084971 Campinas, SP, Brazil

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 15期

关键词：

ACROMELIC ACID; AMINO-ACIDS; KAINIC ACID; DEAROMATISING CYCLIZATION; ALPHA-ALLOKAINOIDS; PALLADIUM; H-1-NMR; ANALOGS;

D O I：

10.1021/ol070980t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Heck arylation of N-carbomethoxy-(L)-3-dehydroproline methyl ester with arenediazonium tetrafluoroborates produced chiral 4-aryldehydroproline derivatives in moderate to good yields in a highly regio- and stereocontrolled fashion. A rationale for the unexpected high regioselectivity is provided using Deeth's model. Heck adduct 15 (G = o-CH3O) was converted into several aryl kainoids using concise and efficient routes.

引用

页码：2815 / 2818

页数：4

共 29 条

[1] Synthesis of a potent (±)-4-(2-hydroxyphenyl) analogue of the acromelic acids by dearomatising cyclisation of a lithiated N-p-methoxybenzyl-4-methoxy-l-naphthamide [J].

Ahmed, A ;

Bragg, RA ;

Clayden, J ;

Tchabanenko, K .

TETRAHEDRON LETTERS, 2001, 42 (20) :3407-3410

[2] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 1: The Heck reaction [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

TETRAHEDRON, 2005, 61 (50) :11771-11835

[3]

[Anonymous], 1995, PALLADIUM REAGENTS C, DOI DOI 10.1021/ol101619s

[4] Stereocontrol in the synthesis of kainoids [J].

Baldwin, JE ;

Fryer, AM ;

Spyvee, MR ;

Whitehead, RC ;

Wood, ME .

TETRAHEDRON LETTERS, 1996, 37 (38) :6923-6924

[5] 1H NMR study of protected and unprotected kainoid amino acids:: Facile assignment of C-4 stereochemistry [J].

Baldwin, JE ;

Fryer, AM ;

Pritchard, GJ .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2597-2601

[6] Dearomatising cyclisation of lithiated l-naphthamides with a phenylglycinol-derived chiral auxiliary: asymmetric synthesis of an arylkainoid and a kainoid-like pyroglutamate [J].

Bragg, RA ;

Clayden, J ;

Bladon, M ;

Ichihara, O .

TETRAHEDRON LETTERS, 2001, 42 (20) :3411-3414

[7] Heck couplings of non-activated alkenes [J].

Crisp, GT ;

Gebauer, MG .

TETRAHEDRON, 1996, 52 (38) :12465-12474

[8] Electronic control of the reglochemistry in palladium - Phosphine catalyzed intermolecular heck reactions [J].

Deeth, RJ ;

Smith, A ;

Brown, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (22) :7144-7151

[9] The double reduction of cyclic sulfonamides for the synthesis of (4S-phenylpyrrolidin-2R-yl)methanol and 2S-methyl-4S-phenylpyrrolidine [J].

Evans, Paul .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (05) :1830-1833

[10] 4-Benzyl-2,3-didehydroprolinate as a homochiral template for Michael additions. Synthesis of enantiopure alpha-allokainoids, beta-Kainoids, 2,3-methanoprolines and other 3,4-disubstituted prolines [J].

Ezquerra, J ;

Escribano, A ;

Rubio, A ;

Remuinan, MJ ;

Vaquero, JJ .

TETRAHEDRON-ASYMMETRY, 1996, 7 (09) :2613-2626

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