Electrodeposition of tin onto a silver textile electrode for Barbier-type electro-organic synthesis of homoallylic alcohols

2021 ◽  
Vol 24 ◽  
pp. 101085
Author(s):  
Sembanadar Karuppusamy ◽  
Frank Marken ◽  
Manickam Anbu Kulandainathan
Keyword(s):  
Organic Synthesis ◽  
Homoallylic Alcohols ◽  
Textile Electrode

Redox-Neutral Propargylic C–H Functionalization by Using Iron Catalysis

Synlett ◽  
2020 ◽  
Vol 31 (18) ◽  
pp. 1747-1752 ◽  
Author(s):  
Yi-Ming Wang ◽  
Austin C. Durham ◽  
Yidong Wang
Keyword(s):  
Organic Synthesis ◽  
Future Directions ◽  
Iron Catalysis ◽  
Homoallylic Alcohols ◽  
Conceptual Background ◽  
Electrophilic Reagents

AbstractIn spite of their rich stoichiometric chemistry, cyclopentadienyliron(II) dicarbonyl complexes are rarely used as catalysts in organic synthesis. Inspired by precedents in the chemistry of cationic olefin complexes and neutral allylmetal species, our group has developed a coupling of alkynes or alkenes with aldehydes and other carbonyl electrophiles to give homopropargylic and homoallylic alcohols, respectively, by using a substituted cyclopentadienyliron(II) dicarbonyl complex as the catalyst. In this article, we first contextualize this development within the conceptual background of C–H functionalization chemistry and relative to key stoichiometric precedents. We then give an account of our group’s discovery and development of the catalytic α-functionalization of alkenes and alkynes with electrophilic reagents.Introduction Preliminary Stoichiometric WorkHydroxyalkylation Development and ScopeConclusions and Future Directions

1993 R.U. Lemieux Award Lecture Organometallic-type reactions in aqueous media—a new challenge in organic synthesis

1994 ◽  
Vol 72 (5) ◽  
pp. 1181-1192 ◽  
Author(s):  
T.H. Chan ◽  
C.J. Li ◽  
M.C. Lee ◽  
Z.Y. Wei
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Organic Solvents ◽  
Carbonyl Compounds ◽  
Aqueous Media ◽  
Coupling Reactions ◽  
Homoallylic Alcohols ◽  
Allyl Halides ◽  
Nonulosonic Acid

The development of organometallic-type reactions in aqueous media is reviewed. Coupling reactions of allyl halides with carbonyl compounds mediated by zinc, or tin, or indium in aqueous media to give homoallylic alcohols are discussed. The stereochemical outcome is compared with similar reactions in organic solvents. A concise synthesis of (+)-muscarine is used to illustrate the usefulness of aqueous organometallic-type reactions in organic synthesis. The procedure to protect–deprotect hydroxy functional groups may not be necessary in these reactions. An application in the carbohydrate area is demonstrated with the synthesis of (+)-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). The mechanistic possibilities of organometallic-type reactions in aqueous media are outlined.

scholarly journals Cobalt-Catalyzed Diastereo- and Enantioselective Allyl Addition to Aldehydes and α-Ketoesters through Allylic C–H Functionalization

2020 ◽  
Author(s):  
Haiyan Zhang ◽  
Jun Huang ◽  
Fanke Meng
Keyword(s):  
Total Synthesis ◽  
Organic Synthesis ◽  
Cobalt Complexes ◽  
Phosphine Ligand ◽  
Catalytic Reactions ◽  
Catalytic Process ◽  
High Demand ◽  
Formal Synthesis ◽  
Homoallylic Alcohols ◽  
Enantioselective Addition

Abstract Catalytic reactions that can generate nucleophilic allyl–metal intermediates directly from simple alkenes without prefunctionalization, and ones that produce various homoallylic alcohols diastereo- and enantioselectively are of great importance in organic synthesis. Transformations that accomplish these two tasks simultaneously are in high demand, particularly if the catalysts, substrates and reagents are inexpensive and easy to access. Here we report a catalytic process that chemoselective formation of nucleophilic allyl–cobalt complexes through oxidative allylic C–H cleavage of alkenes followed by site-, diastereo- and enantioselective addition to aldehydes and α-ketoesters. The enantioenriched products that are otherwise difficult to access are obtained in up to 96% yield, with >95:5 dr and 98:2 er. The cobalt-based catalyst is derived from a commercially available chiral phosphine ligand. The utility of the method is demonstrated through enantioselective formal synthesis of lithospermic acid and total synthesis of dihydrodehydrodiconiferylalcohol.

Modern Methods of Organic Synthesis

2004 ◽  
Author(s):  
W. Carruthers ◽  
Iain Coldham
Keyword(s):  
Organic Synthesis ◽  
Modern Methods
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