期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 34, 页码 12161-12165出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja506885s
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资金
- National Institutes of Health (National Institute of General Medical Sciences) [R01-GM62871]
- Kwanjeong Educational Foundation
- MICINN
- Gordon and Betty Moore Foundation
The development of efficient methods for the generation of enantioenridied sulfonamides and sulfones is an important objective for fields such as organic synthesis and medicinal chemistry; however, there have been relatively few reports of direct catalytic asymmetric approaches to controlling the stereochemistry of the sulfur-bearing carbon of such targets. In this report, we describe nickel-catalyzed stereo-convergent Negishi arylations and alkenylations of racemic alpha-bromosulfonamides and -sulfones that furnish the desired cross-coupling product in very good ee and yield for an array of reaction partners. Mechanistic studies are consistent with the generation of a radical intermediate that has a sufficient lifetime to diffuse out of the solvent cage and to cyclize onto a pendant olefin.
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