Asymmetric cycloadditions of o-quinone methides employing chiral ammonium fluoride precatalysts.

ABSTRACT: The catalytic, enantioselective, [4 + 2] cycloaddition reaction of ortho-quinone methides with silyl ketene acetals is described. This mechanistically interesting reaction, initiated by a chiral cinchona alkaloid-derived ammonium fluoride "precatalyst" complex, affords a variety of alkyl- and aryl-substituted 3,4-dihydrocoumarin products in excellent yield and with good enantioselectivity.

SUBMITTER: Alden-Danforth E 

PROVIDER: S-EPMC2652256 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature