138723-71-4Relevant articles and documents
Magnesium bistrifluoromethanesulfonimide catalysed three-component synthesis of protected homoallylic amines
Wang, Hongshe,Zhao, Weixing
, p. 310 - 312 (2011)
A one-pot, three-component reaction of an aldehyde, benzyl carbamate and allyltrimethylsilane in the presence of 3 mol% of magnesium bistrifluoromethanesulfonimide at room temperature has been shown to afford the corresponding protected homoallylic amine in high yield.
FeSO4·7H2O-catalyzed four-component synthesis of protected homoallylic amines
Song, Qi-Yi,Yang, Bai-Ling,Tian, Shi-Kai
, p. 5407 - 5410 (2007)
(Chemical Equation Presented) An efficient catalytic four-component reaction of carbonyl compounds (or acetals/ketals), benzyl chloroformate (CbzCl), 1,1,1,3,3,3-hexamethyldisilazane (HMDS), and allyltrimethylsilane has been successfully developed to produce Cbz-protected homoallylic amines in the presence of 5 mol % of iron(II) sulfate heptahydrate (FeSO4· 7H2O), an inexpensive and environmentally friendly catalyst, at room temperature.
Highly efficient three-component synthesis of protected homoallylic amines by bismuth triflate-catalyzed allylation of aldimines
Ollevier, Thierry,Ba, Tuya
, p. 9003 - 9005 (2003)
Bismuth triflate catalyzes the allylation of a variety of in situ generated protected aldimines using aldehydes, primary carbamates, and allyltrimethylsilane in a three-component reaction. The reaction proceeds rapidly and affords the corresponding protected homoallylic amine in good yield (up to 86%). Scope and limitations of the aldehyde and carbamate components are reported.
The first catalytic Sakurai reaction of N-alkoxycarbonylamino sulfones with allyltrimethylsilane
Ollevier, Thierry,Li, Zhiya
, p. 4440 - 4443 (2006)
The first Sakurai reaction of N-benzyloxycarbonylamino sulfones with allyltrimethysilane in the presence of a catalytic amount of Bi(OTf) 3.4H2O was investigated. Several solvents were screened for the Sakurai reaction and N-benzylox
Modular synthesis of the pyrimidine core of the manzacidins by divergent Tsuji-Trost coupling
Bretzke, Sebastian,Scheeff, Stephan,Vollmeyer, Felicitas,Eberhagen, Friederike,Rominger, Frank,Menche, Dirk
, p. 1111 - 1121 (2016/07/06)
The design, development and application of an efficient procedure for the concise synthesis of the 1,3-syn- and anti-tetrahydropyrimidine cores of manzacidins are reported. The intramolecular allylic substitution reaction of a readily available joint urea-type substrate enables the facile preparation of both diastereomers in high yields. The practical application of this approach is demonstrated in the efficient and modular preparation of the authentic heterocyclic cores of manzacidins, structurally unique bromopyrrole alkaloids of marine origin. Additional features of this route include the stereoselective generation of the central amine core with an appending quaternary center by an asymmetric addition of a Grignard reagent to a chiral tert-butanesulfinyl ketimine following an optimized Ellman protocol and a cross-metathesis of a challenging homoallylic urea substrate, which proceeds in good yields in the presence of an organic phosphoric acid.
HBF4·OEt2: An efficient fluorinated acid catalyst for the one-pot synthesis of secondary and tertiary N-homoallylic carbamates
Baishya, Gakul,Hazarika, Nabajyoti,Sarmah, Barnali
, p. 1 - 7 (2014/12/10)
An efficient method for the one-pot synthesis of secondary and tertiary N-homoallylic carbamates using catalytic amount of HBF4·OEt2is described. The reaction proceeded smoothly to afford the corresponding N-homoallylic carbamates in good to high yields. Operationally simple and easily scalable features make this method more practical over existing methods. Use of HBF4·OEt2as an acid catalyst also proves the catalytic activity of fluorinated acid catalyst in this important organic transformation.
