Asymmetric Diels-Alder reactions of 5-substituted and 5,6-disubstituted (S)-2-(p-tolylsulfinyl)-1,4-benzoquinones with cyclopentadiene and trans-piperylene

Authors
Carreno, MC Ruano, JLG Lafuente, C Toledo, MA
Citation
Mc. Carreno et al., Asymmetric Diels-Alder reactions of 5-substituted and 5,6-disubstituted (S)-2-(p-tolylsulfinyl)-1,4-benzoquinones with cyclopentadiene and trans-piperylene, TETRAHEDR-A, 10(6), 1999, pp. 1119-1128
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
6
Year of publication
1999
Pages
1119 - 1128
Database
ISI
SICI code
0957-4166(19990326)10:6<1119:ADRO5A>2.0.ZU;2-G
Abstract
A systematic study of reactions between 5-substituted and 5,6-disubstituted (S)-2-p-tolylsulfinyl-p-benzoquinones and cyclopentadiene or trans-piperyl ene is reported. Complete regio and pi-facial selectivities are observed. T he different behaviours of cyclic and acyclic dienes in the presence of ZnB r2 (cyclopentadiene showed reversed diastereoselection) and the role of BF3 . OEt2 are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.