Photoredox/Cobalt Dual‐Catalyzed Decarboxylative Elimination of Carboxylic Acids: Development and Mechanistic Insight
作者:Kaitie C. Cartwright、Ebbin Joseph、Chelsea G. Comadoll、Jon A. Tunge
DOI:10.1002/chem.202001952
日期:2020.9.25
Recently, dual‐catalytic strategies towards the decarboxylative elimination of carboxylicacids have gained attention. Our lab previously reported a photoredox/cobaloxime dual catalytic method that allows the synthesis of enamides and enecarbamates directly from N‐acyl amino acids and avoids the use of any stoichiometric reagents. Further development, detailed herein, has improved upon this transformation's
Stereoselective reduction of α-alkoxy acetylenic ketones with zinc borohydride and K-selectride.
作者:Takashi Takahashi、Masahiro Miyazawa、Jiro Tsuji
DOI:10.1016/s0040-4039(00)98885-3
日期:1985.1
Reduction of α-benzyloxy acetylenic ketones with zincborohydride afforded the erythro-acetylenic vicinal diols in 95% stereoselectivity, while reduction with K-selectride gave the isomeric threo-diols in 90% stereoselectivity.
Scope and stereochemistry of an olefin synthesis from β-hydroxysulphones
作者:Philip J. Kocienski、Basil Lythgoe、Steven Ruston
DOI:10.1039/p19780000829
日期:——
The synthesis of olefinsfrom β-acyloxy-sulphones by reduction with sodium amalgam in methanol–ethyl acetate can be applied to the preparation of a wide variety of conjugated dienes. When used for the synthesis of 1,2-disubstituted olefins in which the new double bond is either isolated or conjugated, the reaction is highly stereoselective, and leads to the trans-isomers.
Stereoselective Negishi-like Couplings Between Alkenyl and Alkyl Halides in Water at Room Temperature
作者:Arkady Krasovskiy、Christophe Duplais、Bruce H. Lipshutz
DOI:10.1021/ol101885t
日期:2010.11.5
Mix in water and then stir. That is all that is required in this new approach to stereoselective sp3−sp2 cross-couplings between an alkyl and alkenyl halide. Prior formation of organozinc reagents is not required.
Electroorganic Synthesis. 65. Anodic Homocoupling of Carboxylic Acids Derived from Fatty Acids.
作者:Andreas Weiper-Idelmann、Martin aus dem Kahmen、Hans J. Schäfer、Marianne Gockeln、Per Halfdan Nielsen、Ask Püschl、Kurt V. Mikkelsen、Alexander Senning
DOI:10.3891/acta.chem.scand.52-0672
日期:——
Fatty acid derived carboxylic acids with double bonds, hydroxy-, amino-, keto-, ester- and epoxy groups are anodically coupled to dimers (Kolbe electrolysis) in 29 to 81% yield and up to a 2.5 mol scale. Problems due to the low conductivity of fatty acid salts were overcome by the use of a how cell with a narrow electrode gap. Fatty acids with branched alkyl chains gave dimers with interesting emulsifying properties. Dimethyl hexadecanedioate, accessible from methyl azelate, could be cyclized and further converted into homomuscone and muscone in a few steps. A commercial mixture of dimeric fatty acids (C-36-dicarboxylic acids) has been coupled to give C-70-diesters.