73082-84-5Relevant academic research and scientific papers
Dramatic Solvent Effects and Stereospecificity in Allylic Sulphinate-Sulphone Rearrangements
Hiroi, Kunio,Kitayama, Ryuichi,Sato, Shuko
, p. 1470 - 1472 (1983)
Dramatic solvent effects were observed in the thermolysis of allyl sulphinates; heating of chiral trans- and cis-allyl sulphinates (S)-(-)-(1a - g) in N,N-dimethylformamide at 90 - 120 deg C provided chiral sulphones (2a - d) in good yields with very high stereospecificity.
Tungsten-Catalyzed Allylic Substitution with a Heteroatom Nucleophile: Reaction Development and Synthetic Applications
Xu, Yaoyao,Salman, Muhammad,Khan, Shahid,Zhang, Junjie,Khan, Ajmal
, p. 11501 - 11510 (2020/10/12)
A tungsten-catalyzed allylic allylation of sodium sulfinate as the heteroatom nucleophile was developed. The reaction utilizes inexpensive and readily available (CH3CN)3W(CO)3 as a precatalyst and proceeds at 60 °C temperature in the presence of 2,2′-bipyridine and its derivatives as ligand. The synthetic utility of allylic sulfones as electrophile was further demonstrated through Suzuki-Miyaura cross-coupling as showcased by the formal synthesis of (±)-hinokiresinol.
Base-promoted coupling of carbon dioxide, amines, and N-tosylhydrazones: A novel and versatile approach to carbamates
Xiong, Wenfang,Qi, Chaorong,He, Haitao,Ouyang, Lu,Zhang, Min,Jiang, Huanfeng
supporting information, p. 3084 - 3087 (2015/05/12)
A base-promoted three-component coupling of carbon dioxide, amines, and N-tosylhydrazones has been developed. The reaction is suggested to proceed via a carbocation intermediate and constitutes an efficient and versatile approach for the synthesis of a wide range of organic carbamates. The advantages of this method include the use of readily available substrates, excellent functional group tolerance, wide substrate scope, and a facile work-up procedure.
Direct transformation of terminal alkynes to branched allylic sulfones
Xu, Kun,Khakyzadeh, Vahid,Bury, Timm,Breit, Bernhard
supporting information, p. 16124 - 16127 (2015/01/09)
A new strategy for the transformation of terminal alkynes to branched allylic sulfones was developed. Using a Rh(I)/DPEphos/benzoic acid catalyst system, terminal alkynes react with sulfonyl hydrazides to produce branched allylic sulfones with good to exc
An unexpected reaction of arenesulfonyl cyanides with allylic alcohols: Preparation of trisubstituted allyl sulfones
Reddy, Leleti Rajender,Hu, Bin,Prashad, Mahavir,Prasad, Kapa
experimental part, p. 172 - 174 (2009/04/10)
(Chemical Equation Presented) An efficient and practical protocol for the highly selective preparation of substituted allyl sulfones has been developed. Arenesulfonyl cyanides, Baylis-Hillman adducts, and simple allylic alcohols give an unforeseen outcome
Studies on Chiral Organo-Sulfur Compounds. II. Stereochemistry of Thermal Chiral Allyl Sulfinate-Sulfone Rearrangements
Hiroi, Kunio,Kitayama, Ryuichi,Sato, Shuko
, p. 2628 - 2638 (2007/10/02)
A highly efficient and general synthetic route to optically active sulfinates by the stereospecific boron trifluoride etherate-catalyzed esterification of sulfinamides was developed.Dramatic solvent effects were observed in the thermal transformation of allyl sulfinate derivatives to sulfones.Heating of chiral trans- and cis-allyl sulfinates, (S)-(-)-3a,c,e and (S)-(-)-3b,d,f, in N,N-dimethylformamide at 90-120 deg C provided chiral sulfones (S)-(+)- and (R)-(-)-5,6,7 in good yields, respectively, with exceedingly high stereospecificity. Keywords - asymmetric transfer; stereospecificity; chiral allyl sulfinate; chiral allyl sulfone; boron trifluoride etherate; thermolysis
