159706-35-1Relevant academic research and scientific papers
Dynamic kinetic resolution of (S)-mandelate-derived a-bromo esters in nucleophilic substitution and asymmetric syntheses of 3-substituted morpholin-2-ones
Lee, Yoon Min,Kang, Kyoung Hee,Min, Hye-Min,Lim, Hyun Jin,Park, Eun-Hyung,Park, Yong Sun
experimental part, p. 1 - 15 (2010/08/06)
Dynamic kinetic resolution of (S)-mandelate-derived α-bromo esters in nucleophilic substitution reaction has been investigated. Substitutions with various alkyl amine nucleophiles in the presence of TBAI and DIEA can provide various α-amino esters up to 81% yield and 97:3 dr. Also, the substitution of α-bromo esters with N-substituted 2-aminoethanol nucleophiles and following spontaneous cyclization provides a practical protocol for asymmetric syntheses of 3-substituted morpholin-2-ones up to 95:5 er. ARKAT USA, Inc.
Simple and efficient one pot synthetic protocol to construct morpholin-2-ones
Yellol, Gorakh S.,Mohapatra, Debendra K.,Gurjar, Mukund K.,Sun, Chung-Ming
experimental part, p. 431 - 439 (2011/05/02)
A new one pot synthetic method to construct 3-substituted morpholine-2-one derivatives is presented. Amino acids refluxed with 1,2-dibromoethane and potassium carbonate in acetonitrile followed by treatment with benzyl bromide in same pot furnished the 3-
An asymmetric synthesis of 3-aryl-1,4-oxazin-2-ones: Synthesis of a key intermediate of an NK1 receptor antagonist
Devine, Paul N.,Foster, Bruce S.,Grabowski, Edward J. J.,Reider, Paul J.
, p. 119 - 123 (2007/10/03)
Pyrrolidine derived (S)-lactamide auxiliaries mediate a highly diastereoselective coupling reaction between racemic α-halo acids and N-benzylethanolamine. The adducts are readily cyclized upon treatment with a catalytic amount of TsOH giving the above tit
Stereoselective synthesis of 2-(S)-(3,5-bis(trifluoromethyl) benzyloxy)-3-(S)-phenyl-1,4-oxazine
Ashwood, Michael S.,Cottrell, Ian F.,Davies, Antony J.
, p. 957 - 963 (2007/10/03)
A convenient process for the preparation of the secondary amine 6, 2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(S)- (3,5-bis(trifluoromethyl)benzyloxy)-3-(S)-phenyl-1,4-oxazine, is described starting from the readily available (S)-phenylglycine 1. The process features efficient construction of the homochiral oxazinone intermediate 3 and stereoselective introduction of the 2-(3,5-bis(trifluoromethyl)-benzyloxy) group by L-Selectride reduction followed by in situ alkylation with the highly reactive 3,5-bis(trifluoromethyl)-benzyl triflate 4.
