Facile and efficient synthesis of homoallylic alcohols using allyl bromide and commercial zinc dust (original) (raw)

Stereospecific synthesis of allylic and homoallylic alcohols from functionalized propargylic alcohols

Arkivoc, 2008

1-Substituted 4,4,5,5-tetraethoxy-2-pentyn-1-ols undergo stereospecific reduction to allylic and homoallylic alcohols under the right conditions. Hydrogenation over Lindlar's catalyst gave the corresponding (Z)-allylic alcohols in excellent yield provided potassium carbonate was added. Reduction was also achieved with lithium aluminum hydride, but the product appeared to be solvent and temperature dependent. In THF at-15 o C the corresponding (E)-allylic alcohols were formed, in better than 70% yield from secondary propargylic alcohols, but below 60% from tertiary ones; in refluxing diethyl ether the products were the corresponding 1-substituted derivatives of homoallylic alcohol (E)-4,5,5-triethoxypent-3-en-1-ol, obtained in 93% yield in the best case.

Metal-Free Synthesis of Homopropargylic Alcohols from Aldehydes

The Journal of Organic Chemistry, 2017

The synthesis of homopropargylic alcohols under metal-free and mild condition is described. This transformation is based on a one-pot procedure involving sequential αalkynylation of acyclic aldehydes using hypervalent iodine reagents and borohydride reduction. The chemistry exhibit broad substrate scope and good scalability, providing a

Conversion of Homoallylic Alcohols with Alkene Protection to the Corresponding Methyl Ketones

Journal of Organic Chemistry, 1999

In the course of a total synthesis of the potent cytotoxic agents tedanolide 1a and 13-deoxy-tedanolide 1b, 2 a good method was needed to carry out two specific transformations, namely, a reversible protection of the alkene of the homoallylic alcohol system 2 and the conversion of the homoallylic alcohol or ether into the methyl ketone 3.

ChemInform Abstract: Metal-Catalyzed Isomerization of Allylic and Propargylic Alcohols in Aqueous Media

ChemInform, 2013

Metal-catalysis in aqueous medium has led in recent years to the development of a huge number of new and greener synthetic methodologies in organic chemistry. Also, the search for organic reactions that proceed with efficiency, selectivity and atom economy has emerged as a prime goal in synthetic chemistry. Among the organic processes that take place with atom economy, isomerization reactions are typical examples because no byproducts are generated. In this regard, the isomerizations of readily accessible allylic and propargylic alcohols, mainly giving carbonyl compounds, provide a simple synthetic route to these very valuable raw materials in organic chemistry. In this review, an overview of the progress achieved on the catalytic isomerization of allylic and propargylic alcohols in environmentfriendly aqueous media will be presented.