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Design and Synthesis of a New Type of Ferrocene-Based Planar Chiral DMAP Analogues. A New Catalyst System for Asymmetric Nucleophilic Catalysis

2005; American Chemical Society; Volume: 70; Issue: 21 Linguagem: Inglês

10.1021/jo050714y

1520-6904

Jimmi Gerner Seitzberg, Carsten Dissing, Inger Søtofte, Per‐Ola Norrby, Mogens Johannsen,

Chemical Synthesis and Reactions

A new first-generation catalyst system for nucleophilic catalysis has been developed. It is based on a planar chiral ferrocene skeleton with either the potent nucleophile 4-(dimethylamino)pyridine (DMAP) or the related 4-nitropyridine N-oxide attached in either the 2- or the 3-position. The syntheses are short, efficient, and enantioselective and X-ray crystal structures of both DMAP-derived catalysts are presented. The DMAP-based catalysts were tested in asymmetric reactions and the 3-derivative 14 showed good activity and a moderate level of enantioselectivity. The sense of induction (selectivity) was studied using molecular modeling and the results pointed at new directions for future generations of catalysts based on this design.