Regiodivergent and Diastereoselective CuH-Catalyzed Allylation of Imines with Terminal Allenes
A copper-catalyzed, chemoselective hydrometalation process enables the use of simple allenes as allylmetal nucleophile surrogates in imine allylation reactions. By modulating the nitrogen-protecting group, either highly branched- or linear-selective addition can be achieved from the same allene. Bot...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Article |
| Published: |
Wiley-Blackwell
2018
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| Online Access: | http://hdl.handle.net/1721.1/113041 https://orcid.org/0000-0003-3875-4775 |
| Summary: | A copper-catalyzed, chemoselective hydrometalation process enables the use of simple allenes as allylmetal nucleophile surrogates in imine allylation reactions. By modulating the nitrogen-protecting group, either highly branched- or linear-selective addition can be achieved from the same allene. Both reactions exhibit excellent diastereoselectivity and broad functional-group tolerance. Preliminary results indicate that good enantioselectivity can also be achieved in the linear-selective reaction. Finally, a mechanistic model for the regiodivergence is proposed on the basis of density functional theory calculations. |
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