A kinetically controlled direct aldol addition of α-chloro thioesters via soft enolization
Herein we report that simple α-chloro thioesters undergo soft enolization and direct aldol addition to aldehydes in the presence of MgBr2·OEt2and i-Pr2NEt. At ?78?°C the reaction proceeds in a kinetically controlled manner
Alfie, Rachel J.,Truong, Ngoc,Yost, Julianne M.,Coltart, Don M.
supporting information
p. 185 - 189
(2016/12/27)
Direct carbon-carbon bond formation via soft enolization: Aldol addition of α-halogenated thioesters
α-Halo thioesters undergo soft enolization and syn-selective direct aldol addition to aldehydes in the presence of MgBr2·OEt 2 and i-Pr2NEt to produce α-halo-β-hydroxy thioesters.
Yost, Julianne M.,Alfie, Rachel J.,Tarsis, Emily M.,Chong, Insun,Coltart, Don M.
supporting information; experimental part
p. 571 - 572
(2011/02/26)
Silica-promoted facile synthesis of thioesters and thioethers: A highly efficient, reusable and environmentally safe solid support
An efficient, mild and rapid procedure for the acylation and alkylation of aromatic and aliphatic thiols mediated on a silica gel surface at room temperature is described. The protocol allows the protection of thiols under neutral heterogeneous conditions without requiring any bases or Lewis acids, and the silica gel used as the promoter can be recycled for several runs without any loss of activity.
Basu, Basudeb,Paul, Susmita,Nanda, Ashis K.
experimental part
p. 767 - 771
(2010/09/05)
Highly enantio- and diastereoselective boron aldol reactions of α-heterosubstituted thioacetates with aldehydes and silyl imines
Boron enolates derived from α-heterosubstituted thioacetates and bearing menthone-derived chiral ligands react with aldehydes to give anti aldols with excellent diastero- and enantiocontrol. Boron enolates derived from tert-butyl α-halothioacetate and bearing menthone-derived chiral ligands react with imines with excellent diastero- and enantiocontrol to give syn α-halo-β-aminothioesters, which can be converted to the corresponding aziridines by simple ring closure during LAH reduction. A key precursor of antibiotics (+)-thiamphenicol and (-)-florfenicol was synthesized.
Gennari, Cesare,Vulpetti, Anna,Pain, Gilles
p. 5909 - 5924
(2007/10/03)
The Invention of Radical Reactions. XXXIII Homologation Reactions of Carboxylic Acids by Radical Chain Chemistry
Various carbon radicals can be generated from carboxylic acids via the corresponding Barton esters.These radicals can be used for the synthesis of longer chain homologues of the original acids.
Barton, Derek H. R.,Chern, Ching-Yuh,Jaszberenyi, Joseph Cs.
p. 407 - 426
(2007/10/02)
A Convenient Method for the Preparation of Thiol Esters