32140-55-9Relevant academic research and scientific papers
Stereochemical studies of the palladium-catalyzed rearrangements of chiral 2-alkynyl sulfinates into chiral allenyl sulfones
Hiroi, Kunio,Kato, Fumiko
, p. 1543 - 1550 (2001)
Palladium-catalyzed reactions of diastereomerically pure chiral 2-alkynyl p-toluenesulfinates under very mild reaction conditions gave both enantiomers of optically active sulfonyl allenes in good yields with high stereospecificity. The stereochemistry of this transformation with the assistance of a palladium catalyst was determined. The conversion rate was measured by the HPLC analysis in accordance with the elapse of the reaction time, and the rather marked difference of the rate was observed between the diastereomeric sulfinates. A novel mechanism for this transformation with palladium catalysts is proposed.
Stereochemistry of palladium-catalyzed asymmetric transformation of chiral 2-alkynyl sulfinates into allenyl sulfones
Hiroi, Kunio,Kato, Fumiko,Nakasato, Hajime
, p. 553 - 554 (1998)
Optically active 2-alkynyl p-toluenesulfinates, possessing chiralily on both the α-carbons of the 2-alkynyl groups and the sulfur atoms of the sulfinates, were readily transformed into chiral allenyl sulfones with high stereospecificity in good yields by treatment with palladium acetate. The stereochemistry of the transformation was determined and the plausible mechanistic pathway is proposed.
Metal-Free C-C Coupling of an Allenyl Sulfone with Picolyl Amides to Access Vinyl Sulfones via Pyridine-Initiated in Situ Generation of Sulfinate Anion
Omer, Humair M.,Liu, Peng,Brummond, Kay M.
, p. 7959 - 7975 (2020/07/15)
Vinyl sulfones are privileged motifs known for their biological activity and synthetic utility. Synthetic transformations to efficiently access high-value compounds with these motifs are desired and sought after. Herein, a new procedure is described to fo
Studies on the Addition of Allyl Oxides to Sulfonylallenes. Preparation of Highly Substituted Allyl Vinyl Ethers for Carbanionic Claisen Rearrangements
Denmark, Scott E.,Harmata, Michael A.,White, Kathleen S.
, p. 4031 - 4042 (2007/10/02)
Thirty-five allyl vinyl ethers bearing an arylsulfonyl anion-stabilizing group have been prepared by addition of allylic alkoxides to (arylsulfonyl)allenes.The allyl vinyl ethers are produced as either β,γ-unsaturated or α,β-unsaturated sulfones depending upon the substitution pattern of the allene and the reaction conditions.A wide variety of substitution patterns are available by using this method.Factors that control the position and stereochemistry of the vinyl ether double bond are discussed.
