99967-64-3Relevant academic research and scientific papers
Copper-catalyzed enantioselective carbenoid insertion into S-H bonds
Zhang, Yong-Zhen,Zhu, Shou-Fei,Cai, Yan,Mao, Hong-Xiang,Zhou, Qi-Lin
supporting information; experimental part, p. 5362 - 5364 (2009/12/08)
An asymmetric carbenoid insertion into S-H bonds catalyzed by copper-chiral spiro bisoxazoline complexes has been developed, in which a series of α-mercaptoesters were produced in high yields with moderate to good enantioselectivities (up to 85% ee); this
A new method for stereocontrolled synthesis of substituted tetrahydrothiophenes
Ponce, Andres Molina,Overman, Larry E.
, p. 8672 - 8676 (2007/10/03)
A variety of substituted 3-acyltetrahydrothiophenes can be prepared with high stereoselectivity in 50-70% yield by acid-promoted condensation of mercapto allylic alcohols 1 (X = S) with aldehydes and ketones. The mercapto allylic alcohol must be substitut
Substitution of 2-(Sulfonyloxy)carboxylates with Oxygene and Sulfur Nucleophiles without Racemization
Burkard, Ulrike,Effenberger, Franz
, p. 1594 - 1612 (2016/06/15)
The ethyl 2-(sulfonyloxy)propionates (S)-1a-c react with phenolates formed from 2 and with carboxylates 8 to give the respective 2-(aryloxy)- (R)-3 and 2-(acyloxy)propionates (R)-9 with inversion of configuration.Due to the high leaving tendency of the triflate group, (S)-1a generally give higher yields of substitution products under milder conditions than the corresponding mesylate (S)-1b and tosylate (S)-1c.In the case of the reaction of malic and succinic acid derivatives only the triflate (S)-10a is converted to the acyloxy compounds (R)-12 with carboxylates 8 atlow temperature (-45 deg C); with the mesylates 10b and the bromide 10d only elimination is observed.Mercaptides and thiophenolates formed from 17 react with (S)-1a-c analogously.With potassium thiocyanate 1a,b react almost exclusively to give the thiocyanate 19; only traces of the corresponding isothiocyanate 20 are obtained.
