1999•Angewandte Chemie International EditionOpen access

A Stable and Recoverable Chiral Ru Lewis Acid: Synthesis, Asymmetric Diels–Alder Catalysis and Structure of the Lewis Acid Methacrolein Complex

Ernst Peter Kündig, Christophe M. Saudan, Gérald H. Bernardinelli

Abstract

Ease of generation, stablity in solution at ambient temperature, high enantioselectivity in Diels–Alder reactions, efficient catalyst recovery, and large rate differences on variation of the anion are all characteristics of the new Ru Lewis acid [CpRu((S,S)-biphop-F)]+ (biphop-F=(C6F5)2POCH2(Ph)CH2(Ph)OP(C6F5)2). The structure of complex 1 (L=methacrolein, Y=SbF6) provides evidence for a cooperative binding of the dienophile by both the Lewis acid and the anion.

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Key concepts: Methacrolein, Lewis acids and bases, Chemistry, Catalysis, Diels–Alder reaction, Chiral Lewis acid, Medicinal chemistry, Lewis acid catalysis