Enantioselective direct aza hetero-Diels-Alder reaction catalyzed by chiral Brønsted acids

Org Lett. 2006 Dec 21;8(26):6023-6. doi: 10.1021/ol062499t.

Abstract

[Structure: see text] 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.