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Synfacts 2015; 11(1): 0069
DOI: 10.1055/s-0034-1379693
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1,2-Amino Alcohols via Asymmetric Hydrogenation

Contributor(s):
Mark Lautens
,
Thomas Johnson
Yuan M.-L, Xie J.-H, * Yang X.-H, Zhou Q.-L. * Nankai University, Tianjin, P. R. of China
Enantioselective Synthesis of Chiral 1,2-Amino Alcohols via Asymmetric Hydrogenation of α-Amino Ketones with Chiral Spiro Iridium Catalysts.

Synthesis 2014;
46: 2910-2916
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

asymmetric hydrogenation - amino alcohols - iridium

Significance

Chiral 1,2-amino alcohols are very commonly found in pharmaceuticals and natural products. Although many methods exist for their synthesis, the present one, based on asymmetric hydrogenation, is notable for its efficiency in terms of enantioselectivity and turnover number (up to 100 000).


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Comment

Excellent yields and enantioselectivities were obtained on a range of aromatic α-amino ketones with a low catalyst loading (0.02 mol%). When an alkyl α-amino ketone was employed, the product was formed in 98% yield, but was nearly racemic. The authors demonstrate the utility and scalability of their method with the synthesis of (R)-phenylephrine hydrochloride, using only 0.001 mol% catalyst (TON = 100 000).


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