INFLUENCE OF THE SULFINYL GROUP ON THE CHEMOSELECTIVITY AND PI-FACIALSELECTIVITY OF DIELS-ALDER REACTIONS OF (S)-2-(P-TOLYLSULFINYL)-1,4-BENZOQUINONE

Authors
CARRENO MC RUANO JLG TOLEDO MA URBANO A REMOR CZ STEFANI V FISCHER J
Citation
Mc. Carreno et al., INFLUENCE OF THE SULFINYL GROUP ON THE CHEMOSELECTIVITY AND PI-FACIALSELECTIVITY OF DIELS-ALDER REACTIONS OF (S)-2-(P-TOLYLSULFINYL)-1,4-BENZOQUINONE, Journal of organic chemistry, 61(2), 1996, pp. 503-509
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
2
Year of publication
1996
Pages
503 - 509
Database
ISI
SICI code
0022-3263(1996)61:2<503:IOTSGO>2.0.ZU;2-K
Abstract
Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-benzoquinone (1a) with cyclic (cyclopentadiene and cyclohexadiene) and acyclic dienes ( 1-[(trimethylsilyl)oxy]-1,3-butadiene and trans-piperylene) under diff erent thermal and Lewis acid conditions are reported. Chemoselectivity (reactions on C-2-C-3 versus C-5-C-6 double bonds) is mainly related to the cyclic (on C-5-C-6) or acyclic (on C-2-C-3) structure of the di ene. The high pi-facial selectivity observed could be controlled by ch oosing adequate experimental conditions.