期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 3, 页码 1599-1604出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202011339
关键词
alkyl– alkyl cross-coupling; enantioselectivety; hydroalkylation; hydrobenzylation; hydropropargylation
资金
- NSFC [21971101, 21801126]
- Guangdong Basic and Applied Basic Research Foundation [2019A1515011976]
- Pearl River Talent Recruitment Program [2019QN01Y261]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
- Thousand Talents Program for Young Scholars
- Shenzhen Nobel Prize Scientists Laboratory Project [C17783101]
This research presents intermolecular regio- and enantioselective formal hydrofunctionalizations of acrylamides, creating a stereogenic center alpha-position to the newly formed C-sp3-C-sp3 bond for the first time. The use of a newly developed chiral ligand enables electronically-reversed formal hydrofunctionalizations, offering an efficient way to obtain diverse enantioenriched amides with a tertiary alpha-stereogenic carbon center.
The development of enantioselective alkyl-alkyl cross-couplings with coinstantaneous formation of a stereogenic center without the use of sensitive organometallic species is attractive yet challenging. Herein, we report the intermolecular regio- and enantioselective formal hydrofunctionalizations of acrylamides, forging a stereogenic center alpha-position to the newly formed C-sp3-C-sp3 bond for the first time. The use of a newly developed chiral ligand enables the electronically-reversed formal hydrofunctionalizations, including hydroalkylation, hydrobenzylation, and hydropropargylation, offering an efficient way to access diverse enantioenriched amides with a tertiary alpha-stereogenic carbon center which is facile to racemize. This operationally simple protocol allows for the anti-Markovnikov enantioselective hydroalkylation, and unprecedented hydrobenzylation, hydropropargylation under mild conditions with excellent functional group compatibility, delivering a wide range of amides with excellent levels of enantioselectivity.
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