Enantioselective Direct Aza Hetero-Diels−Alder Reaction Catalyzed by Chiral Brønsted Acids
Authors:
- 24 November 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (26) , 6023-6026
Abstract
The first chiral Brønsted acid-catalyzed asymmetric direct aza hetero-Diels−Alder reaction has been described. The phosphoric acids, prepared from binol and H8-binol derivatives, have shown catalytic ability for the reaction of cyclohexenone with N-PMP-benzaldimine. A chiral phosphoric acid, derived from 3,3-di(4-chloropheneyl)-H8-binol, exhibited superior enantioselectivity, affording fairly good yields and enantioselectivities for the reaction of a range of aromatic aldimines with cyclohexenone.Keywords
This publication has 32 references indexed in Scilit:
- Catalytic asymmetric aza Diels–Alder reactions of hydrazones using a chiral zirconium catalystTetrahedron Letters, 2005
- Chiral Copper Complexes of Phosphino Sulfenyl Ferrocenes as Efficient Catalysts for Enantioselective Formal Aza Diels−Alder Reactions of N-Sulfonyl IminesJournal of the American Chemical Society, 2003
- Efficient and Practical Ag-Catalyzed Cycloadditions between Arylimines and the Danishefsky DieneJournal of the American Chemical Society, 2003
- Catalytic Asymmetric Hetero-Diels–Alder Reactions of Carbonyl Compounds and Imines2000
- Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids (1998 to 1999)Natural Product Reports, 2000
- Chiral Catalyst Optimization Using Both Solid-Phase and Liquid-Phase Methods in Asymmetric Aza Diels−Alder ReactionsOrganic Letters, 2000
- A Switch of Enantiofacial Selectivities Using Designed Similar Chiral Ligands in Zirconium-Catalyzed Asymmetric Aza Diels−Alder ReactionsThe Journal of Organic Chemistry, 1999
- The First Enantioselective Aza-Diels-Alder Reactions of Imino Dienophiles on Use of a Chiral Zirconium CatalystAngewandte Chemie International Edition, 1998
- Asymmetric routes to substituted piperidinesChemical Communications, 1998
- Asymmetric aza-Diels-Alder reaction mediated by chiral boron reagentThe Journal of Organic Chemistry, 1992