172376-40-8Relevant articles and documents
Synthesis of 1,3-Amino Alcohols, 1,3-Diols, Amines, and Carboxylic Acids from Terminal Alkynes
Zeng, Mingshuo,Herzon, Seth B.
, p. 8604 - 8618 (2015/09/15)
The half-sandwich ruthenium complexes 1-3 activate terminal alkynes toward anti-Markovnikov hydration and reductive hydration under mild conditions. These reactions are believed to proceed via addition of water to metal vinylidene intermediates (4). The functionalization of propargylic alcohols by metal vinylidene pathways is challenging owing to decomposition of the starting material and catalytic intermediates. Here we show that catalyst 2 can be employed to convert propargylic alcohols to 1,3-diols in high yield and with retention of stereochemistry at the propargylic position. The method is also amenable to propargylic amine derivatives, thereby establishing a route to enantioenriched 1,3-amino alcohol products. We also report the development of formal anti-Markovnikov reductive amination and oxidative hydration reactions to access linear amines and carboxylic acids, respectively, from terminal alkynes. This chemistry expands the scope of products that can be prepared from terminal alkynes by practical and high-yielding metal-catalyzed methods.
Symmetrie macrocycles by a prins dimerization and macrocyclization strategy
Gesinski, Michael R.,Tadpetch, Kwanruthai,Rychnovsky, Scott D.
body text, p. 5342 - 5345 (2010/02/28)
A tandem dimerization/macrocyclization reaction utilizing the Prins cyclization has been developed. This reaction develops molecular complexity through the formation of highly substituted dimeric tetrahydropyran macrocycles. Mild conditions utilizing rhen
SmI2-INDUCED HIGHLY REGIOSELECTIVE REDUCTION OF α,β-EPOXY ESTERS AND γ,δ-EPOXY-α,β-UNSATURATED ESTERS. AN EFFICIENT ROUTE TO OPTICALLY ACTIVE β-HYDROXY AND δ-HYDROXY ESTERS
Otsubo, Kenji,Inanaga, Junji,Yamaguchi, Masaru
, p. 4437 - 4440 (2007/10/02)
α,β-Epoxy esters were rapidly reduced at room temperature to yield β-hydroxy esters with retention of the configurations at the β-carbon atoms by using SmI2-THF-HMPA system in the presence of N,N-dimethylaminoethanol (DMAE).The conditions were successfully applied to the synthesis of vinylogous δ-hydroxy esters.
