Issue 13, 2014

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

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

Supplementary files

Article information

Article type
Communication
Submitted
03 Jan 2014
Accepted
29 Jan 2014
First published
30 Jan 2014

Org. Biomol. Chem., 2014,12, 2049-2052

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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