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Enantioselective aza-Diels–Alder reaction of Brassard’s diene with aldimines catalyzed by chiral N,N′-dioxide–Yb(OTf)3 complex
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Jun2010, Vol. 51 Issue 23, p3088-3091. 4p. - Publication Year :
- 2010
-
Abstract
- Abstract: The chiral N,N′-dioxide–Yb(OTf)3 complex-catalyzed enantioselective aza-Diels–Alder reaction of Brassard’s diene with aldimines has been developed, giving the corresponding α,β-unsaturated δ-lactam derivatives in moderate yields with good enantioselectivities (up to 81% ee and up to 99% ee by single recrystallization) under mild conditions. Isolation of the reaction intermediate indicates that this asymmetric aza-Diels–Alder reaction proceeds through a stepwise Mannich-type pathway. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 51
- Issue :
- 23
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 50391277
- Full Text :
- https://doi.org/10.1016/j.tetlet.2010.04.009