Asymmetric synthesis of cis-2,4-disubstituted azetidin-3-ones from metal carbene chemistry

被引：19

作者：

Burtoloso, ACB ^{[1
]}

Correia, CRD ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2005年 / 690卷 / 24-25期

基金：

巴西圣保罗研究基金会;

关键词：

metal carbenes; azetidines; azetidin-3-ones; N-H insertion; diazoketones;

D O I：

10.1016/j.jorganchem.2005.07.016

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Several chiral cis-2,4-disubstituted azetidin-3-ones were prepared as single diastereoisomers from N-protected amino acids, employing a highly stereoselective copper carbenoid N-H insertion reaction of diazoketones. These azetidin-3-ones were then converted into fully substituted azetidines in a few steps in good to high yields. (c) 2005 Elsevier B.V. All rights reserved.

引用

页码：5636 / 5646

页数：11

共 45 条

[1] PENAZETIDINE-A, AN ALKALOID INHIBITOR OF PROTEIN-KINASE-C [J].

ALVI, KA ;

JASPARS, M ;

CREWS, P ;

STRULOVICI, B ;

OTO, E .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (20) :2447-2450

[2] CATALYTIC ASYMMETRIC-SYNTHESIS OF CYCLOPROPANE-CARBOXYLIC ACIDS - AN APPLICATION OF CHIRAL COPPER CARBENOID REACTION [J].

ARATANI, T .

PURE AND APPLIED CHEMISTRY, 1985, 57 (12) :1839-1844

[3] Metal carbene N-H insertion of chiral α,α′-dialkyl α-diazoketones.: A novel and concise method for the stereocontrolled synthesis of fully substituted azetidines [J].

Burtoloso, ACB ;

Correia, CRD .

TETRAHEDRON LETTERS, 2004, 45 (17) :3355-3358

[4] Stereoselective synthesis of the conformationally constrained glutamate analogue, (-)-(2R,3S)-cis-2-carboxyazetidine-3-acetic acid, from (S)-N-tosyl-2-phenylglycine [J].

Burtoloso, ACB ;

Correia, CRD .

SYNLETT, 2005, (10) :1559-1562

[5] Synthesis of enantiopure 2-acyl azetidines and the application of amino alcohols derived therefrom in enantioselective catalysis [J].

Couty, F ;

Prim, D .

TETRAHEDRON-ASYMMETRY, 2002, 13 (23) :2619-2624

[6] Synthesis of chiral non racemic azetidines [J].

Couty, F ;

Evano, G ;

Prim, D .

MINI-REVIEWS IN ORGANIC CHEMISTRY, 2004, 1 (02) :133-148

[7]

CRAIG D, 1992, SYNLETT, P41

[8] Asymmetric synthesis of cis-5-tert-butylproline with metal carbenoid NH insertion [J].

Davis, FA ;

Yang, B ;

Deng, JH .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) :5147-5152

[9] The chemistry of azetidin-3-ones, oxetan-3-ones, and thietan-3-ones [J].

Dejaegher, Y ;

Kuz'menok, NM ;

Zvonok, AM ;

De Kimpe, N .

CHEMICAL REVIEWS, 2002, 102 (01) :29-60

[10] Synthesis of α-amino-α′-diazomethyl ketones via ring opening of substituted cyclopropanones with alkyl azides.: A facile route to N-substituted 3-azetidinones [J].

Desai, P ;

Aubé, J .

ORGANIC LETTERS, 2000, 2 (12) :1657-1659

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