PI-FACIAL DIASTEREOSELECTION IN DIELS-ALDER REACTIONS OF (R)-4-[(P-TOLYLSULFINYL)METHYL]QUINOLS

Authors
CARRENO MC GONZALEZ MP HOUK KN
Citation
Mc. Carreno et al., PI-FACIAL DIASTEREOSELECTION IN DIELS-ALDER REACTIONS OF (R)-4-[(P-TOLYLSULFINYL)METHYL]QUINOLS, Journal of organic chemistry, 62(26), 1997, pp. 9128-9137
Citations number
44
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
26
Year of publication
1997
Pages
9128 - 9137
Database
ISI
SICI code
0022-3263(1997)62:26<9128:PDIDRO>2.0.ZU;2-X
Abstract
Diels-Alder reactions of a range of -4-[(p-tolylsulfinyl)methyl]-2,5-c yclohexadienones with cyclopentadiene and 1,3-pentadiene proceed in a total pi-facial diastereoselective manner from the C-4 OH side. Ab ini tio calculations at the RHF/6-31G theory level provide data on transi tion-state energies for cycloadditions with cyclopentadiene in full ag reement with the experimental results.