DIELS-ALDER REACTION OF RACEMIC BETA-ISOPROPYL-ALPHA-METHYLENE-BETA-LACTONE WITH ENANTIOMERICALLY PURE 5,6,7,7A-TETRAHYDRO-7A-METHYL-1-PHENYL-4H-INDENE AND RETRO-CLEAVAGE OF THE RESULTING SPIRO-BETA-LACTONES - THE 1ST CASE OF A PERFECT TOPOLOGICAL RESOLUTION

被引：10

作者：

ADAM, W

SALGADO, VON

WEGENER, B

WINTERFELDT, E

机构：

[1] UNIV HANNOVER,INST UROL,SCHNEIDERBERG 1B,W-3000 HANNOVER,GERMANY

[2] UNIV WURZBURG,INST UROL,W-8700 WURZBURG,GERMANY

来源：

CHEMISCHE BERICHTE-RECUEIL | 1993年 / 126卷 / 06期

关键词：

ENANTIOSELECTIVITY; DIELS-ALDER REACTIONS; SPIRO-BETA-LACTONES; RETRO CLEAVAGE; RESOLUTION; TOPOLOGICAL;

D O I：

10.1002/cber.19931260638

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The racemic beta-isopropyl-alpha-methylene-beta-lactone 1 undergoes a configuration-dependent, highly selective [4 + 2] cycloaddition to the enantiomerically pure cyclopentadiene 2; chromatographic separation of the adducts and subsequent thermal retro cleavage provide the pure enantiomers (S)-1 and (R)-1 in 99% e.e.

引用

页码：1509 / 1510

页数：2

共 10 条

[1] ALPHA-METHYLENE-BETA-LACTONE, A NOVEL HETEROCYCLIC RING-SYSTEM VIA DEOXYGENATION OF ALPHA-METHYLENE-BETA-PEROXYLACTONES WITH TRIPHENYLPHOSPHANE
ADAM, W
HASEMANN, L
PRECHTL, F
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1988, 27 (11) : 1536 - 1537
[2] ALPHA-METHYLENE BETA-LACTONES AS MASKED ALLENES AND ALLENE EQUIVALENTS - SOME SELECTED CHEMICAL-TRANSFORMATIONS
ADAM, W
ALBERT, R
HASEMANN, L
SALGADO, VON
NESTLER, B
PETERS, EM
PETERS, K
PRECHTL, F
VONSCHNERING, HG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) : 5782 - 5785
[3] ALPHA-METHYLENE BETA-S-THIOLACTONES - SYNTHESIS OF A NEW HETEROCYCLE BY SULFURIZATION OF AN ALPHA-METHYLENE BETA-LACTONE AND ITS STRUCTURE
ADAM, W
HASEMANN, L
[J]. CHEMISCHE BERICHTE, 1990, 123 (06) : 1449 - 1451
[4] STEREOSELECTIVE SYNTHESIS OF ALPHA,BETA-TRANS-SPIRO-BETA-LACTONES BY DIELS-ALDER CYCLOADDITION OF 1,3-DIENES TO ALPHA-METHYLENE-BETA-LACTONE AND THEIR DECARBOXYLATION BY PYROLYSIS TO (E)-ALKYLIDENECYCLOALKENES, A CONVENIENT OLEFINATION METHOD
ADAM, W
SALGADO, VON
PETERS, EM
PETERS, K
VONSCHNERING, HG
[J]. CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (06): : 1481 - 1486
[5] SYNTHESIS OF ALPHA-METHYLENE BETA-LACTONES, NOVEL HETEROCYCLES
ADAM, W
ALBERT, R
GRAU, ND
HASEMANN, L
NESTLER, B
PETERS, EM
PETERS, K
PRECHTL, F
VONSCHNERING, HG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) : 5778 - 5781
[6] [Anonymous], 1988, ANGEW CHEM, V100, P1594
[7] SYNTHESIS OF ALLENES VIA THERMAL CYCLOREVERSION OF ALPHA-ALKYLIDENE-BETA-LACTONES
DANHEISER, RL
CHOI, YM
MENICHINCHERI, M
STONER, EJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) : 322 - 327
[8] READY ACCESS TO ALPHA-(TRIORGANOSILYL)METHYLENE BETA-LACTONES BY MEANS OF RHODIUM-CATALYZED CYCLOCARBONYLATION OF SUBSTITUTED PROPARGYL ALCOHOLS
MATSUDA, I
OGISO, A
SATO, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (16) : 6120 - 6121
[9] KINETIC RESOLUTION IN DIELS-ALDER PROCESSES
WEGENER, B
HANSEN, M
WINTERFELDT, E
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (03) : 345 - 350
[10] HIGHLY SELECTIVE HIGH-PRESSURE CYCLOADDITIONS
WINTERFELDT, E
WRAY, V
[J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (09): : 2159 - 2161

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