Stereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones

Title
Stereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones
Authors
최준원Pablo Martin-GagoGregory C. Fu
Issue Date
2014-08
Publisher
Journal of the American Chemical Society
Citation
VOL 136, NO 34-12165
Abstract
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.
URI
http://pubs.kist.re.kr/handle/201004/67121
ISSN
0002-7863
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KIST Publication > Article
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