ChemInform Abstract: A Novel Synthesis of Enantiopure Octahydropyrrolo[3,4-b]pyrroles by Intramolecular [3 + 2] Dipolar Cycloaddition on Chiral Perhydro-1,3-benzoxazines.
- Pedrosa, Rafael 1
- Andres, Celia 1
- de las Heras, Laura 1
- Nieto, Javier 1
-
1
Universidad de Valladolid
info
ISSN: 0931-7597, 1522-2667
Year of publication: 2010
Volume: 33
Issue: 47
Pages: no-no
Type: Article
More publications in: ChemInform
Abstract
1,3-Oxazine derivatives (II), obtained as singlediastereomers from (-)-8-aminomenthol via condensation with glycolaldehydedimer, alkylation of the resulting 2-hydroxymethyl perhydrobenzoxazineproduct with alkenyl bromides, and Swern oxidation of the alcohols, affordwith glycine derivatives (III) and (VIII) the cycloadducts (IV) and (IX) withcomplete regio- and diastereoselectivity. It is assumed that the cycloadductsare formed via condensation of oxazines (II) with the glycines, followed bydecarboxylation to provide azomethine ylides, and final intramolecular [3 + 2]cycloaddition. The yields are dependent on the reaction temperature and thepresence or absence of a base. The menthol moiety of compound (IV) is cleavedto afford fused pyrrole (VII).
Bibliographic References
- Pedrosa, (2002), Org. Lett., 4, pp. 2513, 10.1021/ol0261377