Cyclopropanation reactions of pyroglutamic acid-derived synthons with akylidene transfer reagents

被引：87

作者：

Zhang, R ^{[1
]}

Mamai, A ^{[1
]}

Madalengoitia, JS ^{[1
]}

机构：

[1] Univ Vermont, Dept Chem, Burlington, VT 05405 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 02期

关键词：

D O I：

10.1021/jo9816109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclopropanation of unsaturated lactams 1 and 3 derived from pyroglutamic acid with nucleophilic alkylidene transfer reagents is investigated. Good-to-modest yields of cyclopropanes were obtained with most sulfur ylides explored. Syn/anti selectivity was found to be dependent on the synthon as well as the sulfur ylide. This cyclopropanation methodology is used in the synthesis of arginine and glutamic acid analogues.

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页码：547 / 555

页数：9

相关论文

共 30 条

[1] (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL FOR ASYMMETRIC-SYNTHESIS [J].

BALDWIN, JE ;

MOLONEY, MG ;

SHIM, SB .

TETRAHEDRON LETTERS, 1991, 32 (10) :1379-1380

[2] 1H-PYRAZOLE-1-CARBOXAMIDINE HYDROCHLORIDE - AN ATTRACTIVE REAGENT FOR GUANYLATION OF AMINES AND ITS APPLICATION TO PEPTIDE-SYNTHESIS [J].

BERNATOWICZ, MS ;

WU, YL ;

MATSUEDA, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2497-2502

[3] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[4] METHYLSULFINYLCARBANION [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :866-&

[5] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+

[6]

COREY EJ, 1967, TETRAHEDRON LETT, P2325

[7]

COREY EJ, 1979, TETRAHEDRON LETT, P399

[8]

FUJIMOTO Y, 1971, J AM CHEM SOC, V93, P3471

[9] The synthesis of enantiopure omega-methanoprolines and omega-methanopipecolic acids by a novel cyclopropanation reaction: The ''flattening'' of proline [J].

Hanessian, S ;

Reinhold, U ;

Gentile, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (17) :1881-1884

[10] PREPARATION AND SYNTHETIC APPLICATIONS OF (DIMETHYLAMINO)PHENYLOXOSULFONIUM METHYLIDE [J].

JOHNSON, CR ;

HAAKE, M ;

SCHROECK, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (22) :6594-&