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113041 |
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|a Liu, Richard Y.
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|a Liu, Richard
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|a Buchwald, Stephen Leffler
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|a Yang, Yang
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|a Yang, Yang
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|a Buchwald, Stephen L.
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|a Liu, Richard
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|a Buchwald, Stephen Leffler
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|a Regiodivergent and Diastereoselective CuH-Catalyzed Allylation of Imines with Terminal Allenes
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|b Wiley-Blackwell,
|c 2018-01-10T15:53:04Z.
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|z Get fulltext
|u http://hdl.handle.net/1721.1/113041
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|a 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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|a National Institutes of Health (U.S.) (GM46059)
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|a National Institutes of Health (U.S.) (GM058160-17S1)
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|a Massachusetts Institute of Technology (Presidential Graduate Fellowship)
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|a Article
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|t Angewandte Chemie International Edition
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