Asymmetric Hydrogenation of Phenylthio Ketones with Chiral Ru(II) Catalysts

Author:

Tranchier Jean-Philippe,Ratovelomanana-Vidal Virginie,Genêt Jean-Pierre,Tong Shaojing,Cohen Theodore

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference12 articles.

1. The Chemistry of Sulfur-Containing Functional Groups; Patai, S., Rappoport, Z. Eds.; Wiley Interscience: New York, 1993. Oae, S. Organic Sulfur Chemistry; CRC Press: Boca Raton, 1991. Chemistry of Organosulfur Compounds; Belen'Kii, L.I., Ed.; Ellis Horwood: New York, 1990. See also Solladié, G. in Advances in Asymmetric Synthesis, G.R. Stephenson, Ed.; Chapman and Hall: London, 1996, pp 60–92.

2. Simpkins, N.S. Sulphones in Organic Synthesis; Pergamon Press: New York, 1993. Carreno, M.C. Chem. Rev. 1995, 95, 1717–1760.

3. Organoalkali compounds by radical anion induced reductive metalation of phenyl thioethers

4. a) Liu, H.; Cohen, T. J. Org. Chem., 1995, 60, 2022–2025. b) compound 5: [α]D +27 (c = 1.72, CHCl3) e.e. 98% ; compound 8: [α]D −36 (c = 2.05, CHCl3) e.e. 97% ; compound 10: [α]D −15 (c =0.83, CHCl3) e.e. 90% ; compound 11: [α]D +2.4 (c = 1.52, CHCl3) e.e. 70%.

5. Reviews of baker's yeast reductions including examples of ketones bearing sulfur groups: Servi, S. Synthesis, 1990, 1–25. Csuk, R.; Glänzer, B.I. Chem. Rev. 1991, 91, 49–97.

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