STEREODIVERGENT DIELS-ALDER REACTIONS EMPLOYING CYCLITOLS AS CHIRAL AUXILIARIES

Authors
AKIYAMA T HORIGUCHI N IDA T OZAKI S
Citation
T. Akiyama et al., STEREODIVERGENT DIELS-ALDER REACTIONS EMPLOYING CYCLITOLS AS CHIRAL AUXILIARIES, Chemistry Letters, (11), 1995, pp. 975-976
Citations number
26
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
11
Year of publication
1995
Pages
975 - 976
Database
ISI
SICI code
0366-7022(1995):11<975:SDRECA>2.0.ZU;2-L
Abstract
The TiCl4 or SnCl4 mediated Diels-Alder reaction of cyclopentadiene an d chiral acryloyl ester derived from chiral cyclitols proceeded with e xcellent diastereoselectivity in Et(2)O via re-face attack of the acry lates. In contrast, interesting changeover of the diastereofacial sele ctivity was observed by use of toluene or hexane as a solvent to affor d the cycloadducts derived from si-face attack of the acrylates.