Issue 8, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
11 feb 2018
Accepted
24 feb 2018
First published
26 feb 2018

Org. Chem. Front., 2018,5, 1284-1287

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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