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Issue 8, 2018
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Copper-catalyzed asymmetric hydroboration of 1,3-enynes with pinacolborane to access chiral allenylboronates

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Abstract

We report a copper-catalyzed enantioselective hydroboration of 1,3-enynes with the catalyst generated from Cu(OAc) and (S,S)-Ph-BPE. A wide range of alkyl- and aryl-substituted 1,3-enynes undergo this asymmetric hydroboration with pinacolborane, yielding the corresponding allenes in good yields with high to excellent enantioselectivities (up to 99% ee). This asymmetric transformation tolerates a variety of reactive groups, such as chloro, bromo, trifluoromethyl ether, siloxy, carboxylic ester and imido functionalities.

Graphical abstract: Copper-catalyzed asymmetric hydroboration of 1,3-enynes with pinacolborane to access chiral allenylboronates

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Article information


Submitted
11 Feb 2018
Accepted
24 Feb 2018
First published
26 Feb 2018

Org. Chem. Front., 2018,5, 1284-1287
Article type
Research Article

Copper-catalyzed asymmetric hydroboration of 1,3-enynes with pinacolborane to access chiral allenylboronates

H. L. Sang, S. Yu and S. Ge, Org. Chem. Front., 2018, 5, 1284
DOI: 10.1039/C8QO00167G

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