Direct enantioselective approach to oxazolo[4,5-e]isoindoles from [(S)R]-1-aminosubstituted-4-(p-tolylsulfinyl)-1,3-butadienes

Authors
Blasco, S Carreno, MC Cid, MB Ruano, JLG Martin, MR
Citation
S. Blasco et al., Direct enantioselective approach to oxazolo[4,5-e]isoindoles from [(S)R]-1-aminosubstituted-4-(p-tolylsulfinyl)-1,3-butadienes, TETRAHEDR-A, 10(18), 1999, pp. 3473-3477
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
18
Year of publication
1999
Pages
3473 - 3477
Database
ISI
SICI code
0957-4166(19990910)10:18<3473:DEATOF>2.0.ZU;2-2
Abstract
The enantioselective construction of [3aS,5aR,8aR,8bR]-1-(p-methoxyphenyl)- 3a,7-dimethyl-3a,5a,8b,8a-tetrahydro-1H-oxazolo[4,5-e]isoindole-2,6,8-trion e is achieved from enantiopure [(S)R]-(1E,3E)-2-methyl-1-(p-methoxyphenyl)a mino-4-(p-tolylsulfinyl)-1,3-butadiene and N-methylmaleimide through a shor t sequence involving a Diels-Alder reaction, a sulfoxide-sulfenate rearrang ement and intramolecular cyclization. (C) 1999 Elsevier Science Ltd. All ri ghts reserved.