L-proline-mediated one-pot synthesis of 3-exomethylene β-lactams via Kinugasa reaction

被引：35

作者：

Basak, A ^{[1
]}

Ghosh, SC ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

SYNLETT | 2004年 / 09期

关键词：

Kinugasa reaction; beta-lactams; isoxazoline; amino acids; proline;

D O I：

10.1055/s-2004-829097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetically important 3-exomethylene beta-lactams 4a-f were obtained in a single step via Cu(I)-mediated cycloaddition between propargyl alcohol/butyn-2-ol and nitrones 2a-d, in the presence of L-proline (Kinugasa reaction).

引用

页码：1637 / 1639

页数：3

共 16 条

[1] SYNTHETIC STUDIES ON TABTOXIN - SYNTHESIS OF A NATURALLY-OCCURRING INHIBITOR OF GLUTAMINE-SYNTHETASE, TABTOXININE-BETA-LACTAM, AND ANALOGS [J].

BALDWIN, JE ;

OTSUKA, M ;

WALLACE, PM .

TETRAHEDRON, 1986, 42 (12) :3097-3110

[2] An asymmetric synthesis of β-lactams:: on the use of chiral oxazolidones in the Kinugasa reaction [J].

Basak, A ;

Ghosh, SC ;

Bhowmick, T ;

Das, AK ;

Bertolasi, V .

TETRAHEDRON LETTERS, 2002, 43 (31) :5499-5501

[3] An enantiospecific nitrone cycloaddition route to 3-hydroxy-2-azetidinones [J].

Basak, A ;

Bdour, HMM ;

Bhattacharya, G .

TETRAHEDRON LETTERS, 1997, 38 (14) :2535-2538

[4] PPL-catalysed hydrolysis of 3,4-disubstituted β-lactams:: Effect of chain length and stereochemistry on the enantioselectivity [J].

Basak, A ;

Bhattacharya, G ;

Bdour, HMM .

TETRAHEDRON, 1998, 54 (23) :6529-6538

[5] Differential effects of stereochemistry and C-4 substituents on the enantioselectivity of PLE and PPL catalysed hydrolysis of 3,4-disubstituted beta-lactams [J].

Basak, A ;

Mahato, T ;

Bhattacharya, G ;

Mukherjee, B .

TETRAHEDRON LETTERS, 1997, 38 (04) :643-646

[6]

BASAK A, 2001, INDIAN J CHEM B, V41, P244

[7]

BHATTACHARYA G, 1997, THESIS INDIAN I TECH

[8] CIS-AZETIDIN-2-ONES AND TRANS-AZETIDIN-2-ONES FROM NITRONES AND COPPER ACETYLIDE [J].

DING, LK ;

IRWIN, WJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (22) :2382-2386

[9] REACTIONS OF COPPER(I) PHENYLACETYLIDE WITH NITRONES [J].

KINUGASA, M ;

HASHIMOTO, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (08) :466-+

[10] Proline-catalyzed asymmetric reactions [J].

List, B .

TETRAHEDRON, 2002, 58 (28) :5573-5590

← 1 2 →