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Synfacts 2015; 11(4): 0385
DOI: 10.1055/s-0034-1380398
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective and Stereodivergent Synthesis of β,β-Diaryl-α-Amino Acids

Contributor(s):
Mark Lautens
,
Charles C. J. Loh
Molinaro C, * Scott JP, * Shevlin M, * Wise C, Ménard A, Gibb A, Junker EM, Lieberman D. Merck & Co. Inc., Rahway, USA and Merck Sharp and Dohme Ltd, Hoddesdon, UK
Catalytic, Asymmetric and Stereodivergent Synthesis of Non-Symmetric β,β-Diaryl-α-Amino Acids.

J. Am. Chem. Soc. 2015;
137: 999-1006
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Publication History

Publication Date:
18 March 2015 (online)

 
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Key words

palladium - rhodium - asymmetric hydrogenation

Significance

The β,β-diarylalanine core is a synthetically useful motif due to its prevalence in bioactive molecules. Merck process chemists demonstrate the elegant utility of asymmetric Rh-catalyzed hydrogenation to access such challenging structures.


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Comment

The authors report a three-step sequence with potential access to all four stereoisomers of the β,β-diarylalanines. A difficult to achieve hydrogenation on a tetrasubstituted olefin was effected using Rh catalysis with a chiral Josiphos ligand.


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