188447-85-0Relevant academic research and scientific papers
O2-Assisted Four-Component Reaction of Vinyl Magnesium Bromide with Chiral N-tert-Butanesulfinyl Imines To Form syn-1,3-Amino Alcohols
Gao, Lu,Luo, Jingfan,Song, Zhenlei,Wang, Runping,Zhang, Hongyun,Zheng, Chunmei
supporting information, p. 24644 - 24649 (2021/10/12)
An O2-assisted, four-component reaction has been developed to synthesize a wide range of syn-1,3-amino alcohols in one step. The reaction proceeds by oxygenation of vinyl magnesium bromide (component-I) with O2 (component-II) to give
Asymmetric thio-Michael/nucleophilic addition domino reaction with chiral N-sulfinimines
Kamimura, Akio,Okawa, Hidenori,Morisaki, Yuki,Ishikawa, Shingo,Uno, Hidemitsu
, p. 3569 - 3572 (2008/02/04)
(Chemical Equation Presented) Optically active N-sulfinimines underwent stereoselective Michael/nucleophilic addition domino reaction triggered by magnesium thiolate to give α-phenylthiomethyl-β-(N-sulfinylamino) esters in high diastereomeric excess. The
Interesting by-products in the synthesis of chiral α- aminophosphinates from enantiopure sulfinimines
Szabó, Andrea,Jászay, Zsuzsa M.,T?ke, László,Petneházy, Imre
, p. 1991 - 1994 (2007/10/03)
A new reaction of enantiopure sulfinimines and ethyl phenylphosphinate is given. Several unexpected products were isolated and identified, their mechanism of formation is proposed.
Asymmetric Synthesis Properties of Sulfinimines (Thiooxime S-Oxides)
Davis, Franklin A.,Reddy, Rajarathnam E.,Szewczyk, Joanna M.,Reddy, G. Venkat,Portonovo, Padma S.,Zhang, Huiming,Fanelli, Dean,Reddy, R. Thimma,Zhou, Ping,Carroll, Patrick J.
, p. 2555 - 2563 (2007/10/03)
Enantiomerically pure sulfinimines (thiooxime S-oxides 10), important building blocks in the asymmetric synthesis of amine derivatives, are prepared in good to excellent yields in one step from aromatic, heteroaromatic, and aliphatic aldehydes. This protocol involves treating commercially available (R)- or (S)-menthyl p-toluenesufinate (Andersen reagent 4) with LiHMDS, followed by the aldehyde, affording (E)-10 exclusively. The sulfinimines 10 are formed via a Peterson-type olefination reaction of silylsulfinamide anion 13 with the aldehyde. Anion 13 is generated by reaction of lithium menthoxide (12a) with bis(trimethylsilyl)sulfinamide 11, which is formed in the reaction of 4 with LiHMDS. The other product formed is O-(trimethylsilyl)menthol (12c), which is isolated in >80% yield for recycling. Two other less efficient methods for the asymmetric synthesis of 10 are discussed: (i) the asymmetric oxidation of sulfenimines 6 with chiral nonracemic oxaziridines and (ii) the reaction of metal aldimines, prepared from nitriles, with 4. All of these protocols fail with ketones.
