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 RETROCLEAVAGE OF THE RESULTING SPIRO-BETA-LACTONES - THE 1ST CASE OF A PERFECT TOPOLOGICAL RESOLUTION

Authors
ADAM W SALGADO VON WEGENER B WINTERFELDT E
Citation
W. Adam et al., 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 RETROCLEAVAGE OF THE RESULTING SPIRO-BETA-LACTONES - THE 1ST CASE OF A PERFECT TOPOLOGICAL RESOLUTION, Chemische Berichte, 126(6), 1993, pp. 1509-1510
Citations number
10
Categorie Soggetti
Chemistry
Journal title
Chemische Berichte → ACNP
ISSN journal
00092940
Volume
126
Issue
6
Year of publication
1993
Pages
1509 - 1510
Database
ISI
SICI code
0009-2940(1993)126:6<1509:DRORB>2.0.ZU;2-H
Abstract
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 o f the adducts and subsequent thermal retro cleavage provide the pure e nantiomers (S)-1 and (R)-1 in 99% e.e.