Journal
ACS CATALYSIS
Volume 11, Issue 14, Pages 8766-8773Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c02299
Keywords
alkenes; alkylation; asymmetric catalysis; nickel; nickel-hydride
Categories
Funding
- NSFC [21822105, 21772087]
- NSF of Jiangsu Province [BK20201245]
- Nanjing University [CXCY19-41]
- programs for high-level entrepreneurial and innovative talents introduction of Jiangsu Province (group program)
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Here, a chiral selective nickel-hydride catalyzed hydroalkylation method is reported for the synthesis of structurally diverse beta-chiral amides from readily accessible beta-alkyl-alpha,beta-unsaturated amides. The regio-reversed hydronickellation process provides a complementary approach to access enantioenriched beta-functionalization amides with a stereocenter at the beta-position.
Here, we report an enantioselective nickel-hydride catalyzed hydroalkylation of readily accessible beta-alkyl-alpha,beta-unsaturated amides to form structurally diverse beta-chiral amides. This process was proposed to proceed through an enantiodifferentiating syn-hydrometalation of nickel hydride, forming chiral alkylnickel at the beta-position in which the regioselectivity is different from that with copper hydride. This regio-reversed hydronickellation process provides a complementary approach to access enantioenriched beta-functionalization amides with a stereocenter at the beta-position.
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