874291-46-0Relevant academic research and scientific papers
Asymmetric Aldol-Tishchenko Reaction of Sulfinimines
Foley, Vera M.,McSweeney, Christina M.,Eccles, Kevin S.,Lawrence, Simon E.,McGlacken, Gerard P.
, p. 5642 - 5645 (2015)
Methods for the preparation of 1,3-amino alcohols and their derivatives containing two stereogenic centers usually involve a two-step installation of the chiral centers. An aldol-Tishchenko reaction of chiral sulfinimines which involves the first reported reduction of a C=N in this type of reaction is described. Two and even three chiral centers can be installed in one synthetic step, affording anti-1,3-amino alcohols in good diastereo- and enantioselectivity.
Diastereoselective Hydrosilylation of N-(tert-Butylsulfinyl)imines Catalyzed by Zinc Acetate
Adamkiewicz, Anna,Mlynarski, Jacek
, p. 1060 - 1065 (2016/03/01)
An efficient zinc-catalyzed diastereoselective hydrosilylation of N-(tert-butylsulfinyl)imines has been developed that does not require the use of ligands or noble metals. A variety of N-(tert-butylsulfinyl)imines were reduced by this protocol in the presence of a catalytic amount of zinc acetate (5 mol-%) to provide the corresponding secondary amines in high yields with excellent diastereoselectivities (up to 98 % de). This experimentally simple catalytic procedure is easily applicable to the synthesis of both aromatic and aliphatic amines by using triethoxysilane as an efficient hydrogen source.
Asymmetric Reduction of tert-Butanesulfinyl Ketimines by N-Heterocyclic Carbene Boranes
Liu, Tao,Chen, Ling-Yan,Sun, Zhihua
, p. 11441 - 11446 (2015/12/01)
N-heterocyclic carbene borane (NHC-borane) based on a triazole core is demonstrated for the first time to be efficient for reduction of a variety of tert-butanesulfinyl ketimines. Up to 95% yield and up to >99% diastereomeric excess were achieved. NHC-borane exhibited excellent activities that are more efficient than or comparable to commonly used reductive reagents such as NaBH4, NaBH3CN, l-selectride, Ru catalyst, or BH3-THF.
A concise and first synthesis of α-aminophosphinates with two stereogenic atoms leading to optically pure α-amino-H-phosphinic acids
Zhang, Dehui,Yuan, Chengye
supporting information; experimental part, p. 6049 - 6052 (2009/05/30)
A highly stereoselective synthesis of ω-aminophosphinates by nucleophilic attack of ethyl diethoxymethylphosphinate to Ellman's N-(tert-butanesulfinyl) ketimines by using Rb2CO3 as a base at room temperature was reported. In the first set of experiments, (S)-(tert-butane-sulfinyl)methyl (p-bromo)phenylketimine (1j) was used as the model compound to study its reaction with ethyl diethoxymethyl-phosphinate. Ethyl diethoxymethyiphosphinate and Rb2CO3 in CH 2Cl2 were placed in a 20 ml, Schienk flask and (5)-N-tert-butanesulfinylketimines 1 were then added at room temperature. The mixture was then stirred for 3-4 d, while being carefully monitored by TLC. The H NMR analysis showed that they have minor differences with shifts at 3.5 and 4.2 ppm, which can be assigned to the diethoxymethyl and the ethoxyl groups of the products.
