Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 11, Pages 3666-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1002636
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Funding
- Takeda Science Foundation
- JSPS postdoctoral fellowship
- [20037010]
- Grants-in-Aid for Scientific Research [20229001, 20685008] Funding Source: KAKEN
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Direct catalytic asymmetric vinylogous reactions of an alpha,beta-unsaturated gamma-butyrolactam as a donor are described. A homodinuclear Ni-2-Schiff base complex promoted a vinylogous Mannich-type reaction of N-Boc imines as well as a vinylogous Michael reaction to nitroalkenes selectively at the gamma-position under simple proton-transfer conditions. Vinylogous Mannich adducts were obtained in 5:1 -> 30:1 dr and 99% ee, and vinylogous Michael adducts were obtained in 16:1 -> 30:1 dr and 93-99% ee.
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