170646-96-5Relevant articles and documents
Asymmetric Inverse-Electron-Demand Oxa-Diels-Alder Reaction of Allylic Ketones through Dienamine Catalysis
Shi, Ming-Lin,Zhan, Gu,Zhou, Su-Lan,Du, Wei,Chen, Ying-Chun
, p. 6480 - 6483 (2016)
A remote β,γ-regioselective asymmetric inverse-electron-demand oxa-Diels-Alder reaction between allylic ketones and α-cyano-α,β-unsaturated ketones has been developed through induced extended dienamine catalysis of a cinchona-derived primary amine. A spectrum of densely substituted dihydropyran frameworks were efficiently produced with excellent enantioselectivity and fair to exclusive diastereoselectivity.
Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides
Liu, Xin,Werner, Thomas
supporting information, p. 1096 - 1104 (2020/12/31)
Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).
Simple Synthesis of Amides via Their Acid Chlorides in Aqueous TPGS-750-M
Shi, Min,Ye, Ning,Chen, Wei,Wang, Hui,Cheung, Chiming,Parmentier, Michael,Gallou, Fabrice,Wu, Bin
supporting information, p. 1543 - 1548 (2020/11/23)
The technology of surfactant chemistry is employed for amide bond construction via the reaction of acyl chlorides with amines in 2 wt % TPGS-750-M aqueous solution. Specifically, this highly efficient method enables a chromatography-free scalable process and recycling of the TPGS-750-M solution.
Efficient cleavage of tertiary amide bonds: Via radical-polar crossover using a copper(ii) bromide/Selectfluor hybrid system
Maruoka, Keiji,Matsumoto, Akira,Wang, Zhe
, p. 12323 - 12328 (2020/12/08)
A novel approach for the efficient cleavage of the amide bonds in tertiary amides is reported. Based on the selective radical abstraction of a benzylic hydrogen atom by a CuBr2/Selectfluor hybrid system followed by a selective cleavage of an N-C bond, an acyl fluoride intermediate is formed. This intermediate may then be derivatized in a one-pot fashion. The reaction proceeds under mild conditions and exhibits a broad substrate scope with respect to the tertiary amide moiety as well as to nitrogen, oxygen, and carbon nucleophiles for the subsequent derivatization. Mechanistic studies suggest that the present reaction proceeds via a radical-polar crossover process that involves benzylic carbon radicals generated by the selective radical abstraction of a benzylic hydrogen atom by the CuBr2/Selectfluor hybrid system. Furthermore, a synthetic application of this method for the selective cleavage of peptides is described. This journal is
