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Synfacts 2015; 11(1): 0061
DOI: 10.1055/s-0034-1379756
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Tandem α-Alkylation–Asymmetric Transfer Hydrogenation of Acetophenones

Contributor(s):
Hisashi Yamamoto
,
Fengtao Zhou
Kovalenko OO, Lundberg H, Hübner D, Adolfsson H * Stockholm University, Sweden
Tandem α-Alkylation/Asymmetric Transfer Hydrogenation of Acetophenones with Primary Alcohols.

Eur. J. Org. Chem. 2014; 6639-6642
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

transfer hydrogenation - alkylation - ruthenium

Significance

The authors present the first example of a direct formation of enantiomerically enriched secondary alcohols from ketones and ­primary alcohols by a tandem α-alkylation–asymmetric transfer hydrogenation process using [Ru(p-cymene)Cl2]2 as catalyst in the presence of an amino acid hydroxy amide as ligand.


 

Comment

Diversely substituted acetophenones were successfully converted into chiral secondary alcohols via the borrowing hydrogen methodology in moderate yields and in moderate to good enantiomeric excess. In this process, primary alcohols served as both alkylating and reducing agents.


 

 


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