2-Thiazolines in organic synthesis. Formation of .beta.-hydroxy aldehydes with protected hydroxy groups. Synthesis of homoallylic alcohols

1975 ◽  
Vol 40 (14) ◽  
pp. 2025-2029 ◽  
Author(s):  
A. I. Meyers ◽  
James L. Durandetta ◽  
Raphael Munavu
Keyword(s):  
Organic Synthesis ◽  
Homoallylic Alcohols ◽  
Hydroxy Aldehydes ◽  
Hydroxy Groups

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

scholarly journals The allylic chalcogen effect in olefin metathesis

2010 ◽  
Vol 6 ◽  
pp. 1219-1228 ◽  
Author(s):  
Yuya A Lin ◽  
Benjamin G Davis
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Chemical Biology ◽  
Positive Influence ◽  
Efficient Synthesis ◽  
Cross Metathesis ◽  
Allyl Sulfide ◽  
Hydroxy Groups ◽  
Allyl Sulfides

Olefin metathesis has emerged as a powerful tool in organic synthesis. The activating effect of an allylic hydroxy group in metathesis has been known for more than 10 years, and many organic chemists have taken advantage of this positive influence for efficient synthesis of natural products. Recently, the discovery of the rate enhancement by allyl sulfides in aqueous cross-metathesis has allowed the first examples of such a reaction on proteins. This led to a new benchmark in substrate complexity for cross-metathesis and expanded the potential of olefin metathesis for other applications in chemical biology. The enhanced reactivity of allyl sulfide, along with earlier reports of a similar effect by allylic hydroxy groups, suggests that allyl chalcogens generally play an important role in modulating the rate of olefin metathesis. In this review, we discuss the effect of allylic chalcogens in olefin metathesis and highlight its most recent applications in synthetic chemistry and protein modifications.

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.

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