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Issue 13, 2014
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Carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins: highly enantioselective and chemoselective access to a chiral benzylmethyl center

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Abstract

A carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins was developed by using a chiral spiro iridium catalyst, providing a highly efficient approach to the compounds with a chiral benzylmethyl center. The carboxy-directed hydrogenation prohibited the isomerization of the terminal olefins, and realized the chemoselective hydrogenation of various dienes. The concise enantioselective syntheses of (S)-curcudiol and (S)-curcumene were achieved by using this catalytic asymmetric hydrogenation as a key step.

Graphical abstract: Carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins: highly enantioselective and chemoselective access to a chiral benzylmethyl center

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Publication details

The article was received on 03 Jan 2014, accepted on 29 Jan 2014 and first published on 30 Jan 2014


Article type: Communication
DOI: 10.1039/C4OB00018H
Citation: Org. Biomol. Chem., 2014,12, 2049-2052
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    Carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins: highly enantioselective and chemoselective access to a chiral benzylmethyl center

    S. Yang, S. Zhu, N. Guo, S. Song and Q. Zhou, Org. Biomol. Chem., 2014, 12, 2049
    DOI: 10.1039/C4OB00018H

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