Direct synthesis of N-sulfinyl- and N-sulfonylimines via copper/<scp>l</scp>-proline-catalyzed aerobic oxidative cascade reaction of alcohols with sulfinamides or sulfonamides
An efficient one-pot synthetic method of N-sulfinyl- and N-sulfonylimines by the condensation of alcohols with sulfinamides or sulfonamides under mild and green conditions has been developed using a combination of CuI, L-proline and TEMPO. This system shows excellent functional group compatibility for a wide range of substrates and affords the corresponding products in good to excellent yields.
Stereocontrolled Aziridination of Imines via a Sulfonium Ylide Route and a Mechanistic Study
作者:Xiao-Fang Yang、Ming-Jie Zhang、Xue-Long Hou、Li-Xin Dai
DOI:10.1021/jo0257389
日期:2002.11.1
temperature. trans-Aziridines were also obtained when imines 1 and sulfinimines 9 were reacted with N,N-dimethylacetamide-2-dimethylsulfonium bromide (7) in the presence of a base, respectively. A mechanistic study showed that the stereochemistry of these reactions was controlled by the reactivity of the imines and ylides. A higher reactivity of imines and ylides favors the formation of cis-aziridines, whereas
Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines
作者:Chung-Yang (Dennis) Huang、Abigail G. Doyle
DOI:10.1021/ja3013825
日期:2012.6.13
A nickel-catalyzedcross-coupling reaction between N-sulfonyl aziridines and organozinc reagents is reported. The catalytic system comprises an inexpensive and air-stable Ni(II) source and dimethyl fumarate as ligand. Regioselective synthesis of β-substituted amines is possible under mild and functional-group-tolerant conditions. The stereoselectivity of the reaction is consistent with a stereoconvergent
报道了 N-磺酰基氮丙啶和有机锌试剂之间的镍催化交叉偶联反应。该催化系统包含廉价且空气稳定的 Ni(II) 源和富马酸二甲酯作为配体。β-取代胺的区域选择性合成在温和和官能团耐受的条件下是可能的。该反应的立体选择性与其中磺酰胺指导 CC 键形成的立体会聚机制一致。
Aziridination of Activated Imines with Monocarbonyl Iodonium Ylides Generated from (<i>Z</i>)-(2-Acetoxyvinyl)iodonium Salts via Ester Exchange: Stereoselective Synthesis of 2-Acylaziridines
作者:Masahito Ochiai、Yutaka Kitagawa
DOI:10.1021/jo982346m
日期:1999.4.1
Monocarbonyliodoniumylides, generated in situ from (Z)-(2-acetoxyvinyl)iodonium salts via an ester exchange reaction with EtOLi, undergo alkylidene transfer reactions to activated imines yielding 2-acylaziridines in good yields. The stereochemical outcome of this aziridination was shown to be dependent on both the activating groups of the imines and the reaction solvents: that is, the aziridination
Ru-Catalyzed Hydrogen Atom Transfer/C–F Bond Cleavage of Difluoroalkyl Diazos with Hantzsch Ester via a Photocatalytic Radical Process
作者:Qian Wang、Jiang Liu、Haibo Mei、Romana Pajkert、Mira Kessler、Gerd-Volker Röschenthaler、Jianlin Han
DOI:10.1021/acs.orglett.2c03268
日期:2022.11.4
reaction of difluoroalkyl diazo compounds with Hantzschester under visible light to achieve the formation of α-fluorovinylphosphonates via a radical process has been developed. Mechanistic experiments and density functional theory calculations reveal that the generation of a carbon radical is directly through the hydrogen atom transfer (HAT) by Hantzschester. This system represents the first example of