,S)-1,1-BIS-ETHOXYCARBONYL-2,2-BIS-P-TOLYLSULFINYL ETHENE - A HIGHLY STEREOSELECTIVE BUT UNEXPECTEDLY UNREACTIVE DIENOPHILE IN ASYMMETRIC DIELS-ALDER REACTIONS

Authors
CARRETERO JC RUANO JLG CABREJAS LMM
Citation
Jc. Carretero et al., ,S)-1,1-BIS-ETHOXYCARBONYL-2,2-BIS-P-TOLYLSULFINYL ETHENE - A HIGHLY STEREOSELECTIVE BUT UNEXPECTEDLY UNREACTIVE DIENOPHILE IN ASYMMETRIC DIELS-ALDER REACTIONS, Tetrahedron : asymmetry, 8(3), 1997, pp. 409-416
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
3
Year of publication
1997
Pages
409 - 416
Database
ISI
SICI code
0957-4166(1997)8:3<409:,E-AHS>2.0.ZU;2-M
Abstract
The synthesis and dienophilic behaviour of ,S)-1,1-bis-ethoxycarbonyl- 2,2-bis-p-tolylsulfinyl ethene with cyclic and acyclic dienes is repor ted. The stereoselectivity is high with cyclopentadiene and complete w ith acyclic dienes, but its reactivity is unexpectedly low, requiring high pressures (13 Kbar) to evolve into the corresponding adducts or t heir pyrolytic sulfinyl elimination products. (C) 1997 Elsevier Scienc e Ltd. All rights reserved.