Synthesis of optically active spiro-β-lactams by cycloadditions to α-alkylidene-β-lactams

被引：59
作者：
Anklam, S [1 ]
Liebscher, J [1 ]
机构：
[1] Humboldt Univ, Inst Chem, D-10115 Berlin, Germany
来源：
TETRAHEDRON | 1998年 / 54卷 / 23期
关键词：
D O I：
10.1016/S0040-4020(98)00296-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New optically active alpha-methylene-beta-lactam 18 and the alpha-ethylidene-beta-lactams 11-E and 11-Z were synthesized and submitted to 1,3-dipolar cycloadditions with diazomethane, 4-methoxybenzonitrile oxide, and diphenylnitrone as well as to epoxidation by dimethyldioxirane. All cycloadditions proceed with complete regioselectivity giving products 20-25 in an anti-fashion with respect to the substituent at the C-4-position of the starting beta-lactam in diastereomeric ratios of about 80:20. Pure optically active compounds could be obtained in almost all cases after chromatography. Unambiguous structure elucidation could be achieved by X-ray crystal analysis and NOE investigations. (C) 1998 Elsevier Science Ltd. All rights reserved.
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收藏
页码：6369 / 6384
页数：16
相关论文
共 34 条
[1]   SULFOXIDES OF PENICILLANATES WITH NON CLASSICAL SUBSTITUENTS IN THE 6-POSITION [J].
ADAM, S ;
ARNOLD, W ;
SCHONHOLZER, P .
TETRAHEDRON, 1983, 39 (15) :2485-2491
[2]   A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].
ADAM, W ;
BIALAS, J ;
HADJIARAPOGLOU, L .
CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377
[3]   SYNTHESIS OF 3-METHYLENEAZETIDIN-2-ONE DERIVATIVES FROM ALPHA-KETO-AMIDES [J].
ADLINGTON, RM ;
BARRETT, AGM ;
QUAYLE, P ;
WALKER, A ;
BETTS, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (03) :605-611
[4]  
Backer H. J., 1963, ORG SYNTH, VIV, P250
[5]   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
[6]   An enantiospecific nitrone cycloaddition route to 3-hydroxy-2-azetidinones [J].
Basak, A ;
Bdour, HMM ;
Bhattacharya, G .
TETRAHEDRON LETTERS, 1997, 38 (14) :2535-2538
[7]   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
[8]   6-SPIROCYCLOPROPYL PENEMS [J].
BATESON, JH ;
GUEST, AW .
TETRAHEDRON LETTERS, 1993, 34 (11) :1799-1802
[9]   SYNTHESIS OF A POTENT BETA-LACTAMASE INHIBITOR-1,1-DIOXO-6-(2-PYRIDYL)METHYLENEPENICILLANIC ACID AND ITS REACTION WITH SODIUM METHOXIDE [J].
CHEN, YL ;
CHANG, CW ;
HEDBERG, K .
TETRAHEDRON LETTERS, 1986, 27 (30) :3449-3452
[10]   1,3-DIPOLAR ADDITION-REACTIONS OF 6-ETHYLIDENEOLIVANIC ACID-DERIVATIVES WITH DIAZOMETHANE AND ACETONITRILE OXIDE [J].
CORBETT, DF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (03) :421-428
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