An anionic condensation and fragmentation approach to substituted 3-pyrrolines

被引：9

作者：

Weeresakare, GM

Xu, Q

Rainier, JD

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

[2] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 49期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(02)02191-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have identified an anionic condensation and fragmentation sequence from the coupling of 7-azabicyclo[2.2.1]heptenones with aldehydes. This reaction leads to the stereoselective formation of disubstituted 3-pyrrolines as are present in a wide array of bioactive molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：8913 / 8915

页数：3

相关论文

共 20 条

[1] Stereochemistry .87. Synthesis of chiral non-racemic 2-arylpyrrolines by a [3+2] cycloaddition route [J].

Balasubramanian, T ;

Hassner, A .

TETRAHEDRON LETTERS, 1996, 37 (32) :5755-5758

[2] Reaction of the lithio-derivative of methoxy allene with SAMP-hydrazones:: Access to enantiopure 3-pyrrolines [J].

Breuil-Desvergnes, V ;

Compain, P ;

Vatèle, JM ;

Goré, J .

TETRAHEDRON LETTERS, 1999, 40 (27) :5009-5012

[3] ENANTIOSPECIFIC SYNTHESIS OF 3-PYRROLINES - A ROUTE TO NOVEL POLYHYDROXYLATED PYRROLIDINES [J].

BURLEY, I ;

HEWSON, AT .

TETRAHEDRON LETTERS, 1994, 35 (38) :7099-7102

[4]

CHAMBERLAIN P, 1979, TETRAHEDRON LETT, V20, P383

[5] Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]heptanes [J].

Chen, ZM ;

Trudell, ML .

CHEMICAL REVIEWS, 1996, 96 (03) :1179-1193

[6] Thirty years of discovering arthropod alkaloids in amphibian skin [J].

Daly, JW .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (01) :162-172

[7] Synthesis of 3-pyrrolines, annulated 3-pyrrolines, and pyrroles from α-Amino allenes [J].

Dieter, RK ;

Yu, H .

ORGANIC LETTERS, 2001, 3 (24) :3855-3858

[8] A convenient method for 3-pyrroline synthesis [J].

Green, MP ;

Prodger, JC ;

Sherlock, AE ;

Hayes, CJ .

ORGANIC LETTERS, 2001, 3 (21) :3377-3379

[9] SOME ACETYLENIC COMPOUNDS [J].

HEATON, CD ;

NOLLER, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) :2948-2949

[10]

Hercouet A, 2002, SYNLETT, P829