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Synfacts 2015; 11(1): 0052
DOI: 10.1055/s-0034-1379758
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cobalt-Catalyzed Asymmetric Hydroboration of Alkenes

Contributor(s):
Hisashi Yamamoto
,
Masahiro Sai
Zhang L, Zuo Z, Wan X, Huang Z * Shanghai Institute of Organic Chemistry, P. R. of China
Cobalt-Catalyzed Enantioselective Hydroboration of 1,1-Disubstituted Aryl Alkenes.

J. Am. Chem. Soc. 2014;
136: 15501-15504
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

hydroboration - oxazolines - cobalt

Significance

A cobalt-catalyzed asymmetric hydroboration of 1,1-disubstituted aryl alkenes is presented. A series of chiral α-alkyl-β-pinacolatoboranes were prepared with exclusive regioselectivities in high yields (up to 98%) with excellent enantioselectivities (up to 99.5% ee).


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Comment

Novel iminopyridine–oxazoline (IPO) ligands are found to be highly efficient in the enantio­selective hydroboration of alkenes under cobalt catalysis. The synthetic utility of this method is demonstrated by the synthesis of naproxen.


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