Enantioselective copper-catalyzed conjugate addition of diethylzinc to enones using new chiral P,N ligands composed of (S)-2-alkyl-2-aminoethylphosphines and α-substituted pyridines

Author:

Morimoto Toshiaki,Yamaguchi Yoichi,Suzuki Masato,Saitoh Akihito

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference27 articles.

1. (a) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135–631;

2. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771–806;

3. (c) Krause, N.; Gerold, B. E. Angew. Chem., Int. Ed. Engl. 1997, 36, 186–204;

4. (d) Krause, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 283–285.

5. As the ligands for nickel complexes, chiral aminoalcohols were employed in the conjugated addition of diethylzinc to acyclic enones such as chalcone and benzylideneacetone; however, relatively large excess loading of ligands (molar ratios of ligands to Ni=2.4∼24) was necessary to achieve high ee of the products: (a) Soai, K.; Hayasaka, T.; Ugajin, S. Chem. Commun. 1989, 516–517; (b) Bolm, C.; Edwald, M.; Felder, M. Chem. Ber. 1992, 125, 1205–1215; (c) de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479–4491; (d) Fujisawa, T.; Itoh, S.; Shimizu, M. Chem. Lett. 1994, 1777–1780.

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