Asymmetric synthesis of L-azetidine-2-carboxylic acid and 3-substituted congeners - Conformationally constrained analogs of phenylalanine, naphthylalanine, and leucine

被引：48

作者：

Hanessian, S ^{[1
]}

Bernstein, N ^{[1
]}

Yang, RY ^{[1
]}

Maguire, R ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 10期

关键词：

D O I：

10.1016/S0960-894X(99)00218-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Enantiopure L-azetidine-2-carboxylic acid, the (3R)-phenyl, (3R)-naphthyl and (3S)-isopropyl analogs were prepared based on a zinc-mediated asymmetric addition of allylic halides to the camphor sultam derivative of glyoxylic acid O-benzyl oxime. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1437 / 1442

页数：6

共 42 条

[31] ELECTROORGANIC CHEMISTRY .97. A FACILE SYNTHESIS OF 2-SUBSTITUTED AZETIDINES [J].

SHONO, T ;

MATSUMURA, Y ;

UCHIDA, K ;

NAKATANI, F .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (08) :3029-3031

[32] Novel chiral dirhodium catalysts derived from aziridine and azetidine carboxylic acid for intermolecular cyclopropanation reactions with methyl phenyldiazoacetate. [J].

Starmans, WAJ ;

Thijs, L ;

Zwanenburg, B .

TETRAHEDRON, 1998, 54 (3-4) :629-636

[33] Azetidine based ligands in boron catalyzed asymmetric Diels-Alder reactions [J].

Starmans, WAJ ;

Walgers, RWA ;

Thijs, L ;

de Gelder, R ;

Smits, JMM ;

Zwanenburg, B .

TETRAHEDRON, 1998, 54 (19) :4991-5004

[34] Enzymatic resolution of methyl N-alkyl-azetidine-2-carboxylates by Candida antarctica lipase-mediated ammoniolysis [J].

Starmans, WAJ ;

Doppen, RG ;

Thijs, L ;

Zwanenburg, B .

TETRAHEDRON-ASYMMETRY, 1998, 9 (03) :429-435

[35] STRUCTURE OF MUGINEIC ACID, A NEW AMINO-ACID POSSESSING AN IRON-CHELATING ACTIVITY FROM ROOTS WASHINGS OF WATER-CULTURED HORDEUM VULGARE L [J].

TAKEMOTO, T ;

NOMOTO, K ;

FUSHIYA, S ;

OUCHI, R ;

KUSANO, G ;

HIKINO, H ;

TAKAGI, SI ;

MATSUURA, Y ;

KAKUDO, M .

PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 1978, 54 (08) :469-473

[36] REACTION OF AZOMETHINE YLIDES WITH SULFUR YLIDES - NOVEL AZETIDINE SYNTHESIS [J].

VAULTIER, M ;

DANIONBOUGOT, R ;

DANION, D ;

HAMELIN, J ;

CARRIE, R .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (20) :2990-2992

[37] PREPARATION OF BETA-LACTAMS FROM AZETIDINE-2-CARBOXYLIC ACIDS AND ESTERS [J].

WASSERMAN, HH ;

LIPSHUTZ, BH ;

TREMPER, AW ;

WU, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (15) :2991-2999

[38] SYNTHESIS OF (+-)-AZETIDINE-2-CARBOXYLIC ACID AND 2-PYRROLIDINONE DERIVATIVES [J].

YAMADA, Y ;

EMORI, T ;

KINOSHITA, S ;

OKADA, H .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1973, 37 (03) :649-652

[39] Facile new method for preparation of optically active protected proline [J].

Yamaguchi, J ;

Ueki, M .

CHEMISTRY LETTERS, 1996, (08) :621-622

[40] Asymmetric Michael addition of malonate anions to prochiral acceptors catalyzed by L-proline rubidium salt [J].

Yamaguchi, M ;

Shiraishi, T ;

Hirama, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3520-3530

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