5877-10-1Relevant academic research and scientific papers
NaOH-promoted thiolysis of oxiranes using 2-[bis(alkylthio)methylene]-3- oxo-N-o-tolylbutanamides as odorless thiol equivalents
Yu, Haifeng,Dong, Dewen,Ouyang, Yan,Wang, Yan,Liu, Qun
, p. 151 - 155 (2008/03/13)
A convenient and efficient protocol for the thiolysis of oxiranes using 2-[bis(alkylthio)methylene]-3-oxo-N-o-tolylbutanamides as thiol equivalents has been developed. Promoted by sodium hydroxide (NaOH) in ethanol at room temperature, the cleavage commences and the generated thiolate anions undergo nucleophilic addition in situ. β-Hydroxy Sulfides were obtained in high yields along with good β-regioselectivity, and trans β-hydroxy Sulfides were also isolated. The thiolysis of one α,β-epoxyketone product with the thiol equivalents was accomplished to afford the corresponding α-carbonyl sulfides in excellent yields. In all the cases, 3-oxo-N-o-tolylbutanamide, the precursor of the thiol equivalents, could be recovered in the novel thiolysis process as a byproduct in good yield. Georg Thieme Verlag Stuttgart.
Stereo- and regioselective thiolysis of 1,2-epoxides in water
Movassagh, Barahman,Soleiman-Beigi, Mohammad
, p. 3239 - 3244 (2008/02/12)
A simple, efficient, stereoselective, and highly regioselective procedure for the synthesis of β-hydroxy sulfides by thiolysis of various 1,2-epoxides in water as a solvent, using no catalyst and under very mild conditions, is described. Copyright Taylor
Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: Versatile synthons for enantiopure β-hydroxy sulfoxides
Singh, Satwinder,Kumar, Subodh,Chimni, Swapandeep Singh
, p. 2457 - 2462 (2007/10/03)
Humicola lanuginosa lipase-catalyzed acylation of β-hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give β-hydroxy sulfoxides in >99% e.e. The effect of substituents on enantioselectivity is discussed.
NEW ROUTE TO THE PREPARATION OF 1,3,2 OXATHIAPHOSPHOLANES 2-SULFIDE DERIVATIVES
Comel, Alain,Kirsch, Gilbert,Paquer, Daniel
, p. 188 (2007/10/02)
5-Substituted 2-alkyl (or aryl, heteroaryl,...)thio 1,3,2 oxathiaphospholanes 2-sulfide 5 are readily accessible by reaction of the triethylammonium salt 1 of a diester of the phosphorotetrathioic acid with appropriate epoxide in the presence of BF3*Et2O as catalyst.
The First Practical Method of Selective Heteroatom-Directed Chlorohydroxylation
Lai, Jin-Yu,Wang, Fu-Song,Guo, Guang-Zhong,Dai, Li-Xin
, p. 6944 - 6946 (2007/10/02)
A new Pd(II)-catalyzed nucleophilic chlorohydroxylation reaction of allylic amines and sulfides was achieved, and the regioselective reaction gives high yields of the chlorohydrin products, which can be transformed into epoxy compounds or aziridine compou
SYNTHESIS OF 1,3,2-OXATHIAPHOSPHOLANE-2-SULFIDE DERIVATIVES
Comel, Alain,Kirsch, Gilbert,Paquer, Daniel
, p. 229 - 234 (2007/10/02)
5-Substituted 2-alkyl (or aryl, heteroaryl, ...)thio-1,3,2-oxathiaphospholane-2-sulfides 5 are readily accessible by reaction of the triethylammonium salt 1 of a diester of the phosphorotetrathioic acid with appropriate epoxides in the presence of BF3/Et2O as catalyst.Key words: BF3/Et2O; cyclisation reaction; NMR; oxathiaphospholane derivatives; oxiranes; phosphorotetrathioic acid; triethylammonium salts.
OXIRANE RING OPENING REACTIONS WITH THIOLS CATALYZED BY LANTHANIDE COMPLEXES
Vougioukas, Angelos E.,Kagan, Henri B.
, p. 6065 - 6068 (2007/10/02)
LnCl3 (Ln = Ce,Sm) and Eu(fod)3 act as Lewis-acid catalysts in stereo- and regioselective epoxide ring opening reactions with thiols under mild conditions in CH2Cl2.
