Organic Letters 2007-01-18

Asymmetric hydrogenation of alpha-chloro aromatic ketones catalyzed by eta6-arene/TsDPEN-ruthenium(II) complexes.

Takeshi Ohkuma, Kunihiko Tsutsumi, Noriyuki Utsumi, Noriyoshi Arai, Ryoji Noyori, Kunihiko Murata

Index: Org. Lett. 9(2) , 255-257, (2007)

Full Text: HTML

Abstract

Asymmetric hydrogenation of various alpha-chloro aromatic ketones with Ru(OTf)(TsDPEN)(eta6-arene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) produces the chiral chlorohydrins in up to 98% ee. This reaction can be conducted even on a 206-g scale. The hydrogenation of an alpha-chloro ketone with a phenol moiety has been utilized for the synthesis of (R)-norphenylephrine without protection-deprotection operations. [reaction: see text].

Related Compounds

  • 2,4'-dichloroaceto...

Related Articles:

Purification and characterization of a yeast carbonyl reductase for synthesis of optically active (R)-styrene oxide derivatives.

2005-01-01

[Biosci. Biotechnol. Biochem. 69(1) , 79-86, (2005)]

Direct Investigation of Covalently Bound Chlorine in Organic Compounds by Solid-State 35Cl NMR Spectroscopy and Exact Spectral Line-Shape Simulations. Perras FA and Bryce DL.

[Angew. Chem. Weinheim Bergstr. Ger. 124(11) , 4303-4306, (2012)]

Modified coumarins. 10. Synthesis of substituted 2-(7-oxofuro [3, 2-g] chromen-6-yl) acetic acids. Nagorichna IV, et al.

[Chem. Nat. Cpds. 39(3) , 253-261, (2003)]

More Articles...