1262022-91-2Relevant academic research and scientific papers
Dihydrooxazine N-Oxide Intermediates as Resting States in Organocatalytic Kinetic Resolution of Functionalized Nitroallylic Amines with Aldehydes
Gurubrahamam, Ramani,Chen, Yan Ming,Huang, Wan-Yun,Chan, Yu-Te,Chang, Hsiang-Kai,Tsai, Ming-Kang,Chen, Kwunmin
, p. 3046 - 3049 (2016)
Kinetic resolution of nitroallylic amines was established using chiral α,α-l-diphenylprolinol silyl ether auxiliary through isolation of the dihydrooxazine N-oxide intermediates. Further hydrolyzing the resting states provided tetrahydropyridines in high chemical yields and high to excellent stereoselectivities (up to >20:1 dr and 98% ee). A detailed mechanistic explanation for stereoselective protonation in the dihydrooxazine was probed computationally. In addition, the probable intermediates in α-halogenation of aldehydes (masked with enamines) were isolated to provide crystallographic evidence.
An efficient Morita-Baylis-Hillman reaction for the synthesis of multifunctional 2-hydroxy-3-nitrobut-3-enoate derivatives
Kuan, Hsuan-Hao,Reddy, Raju Jannapu,Chen, Kwunmin
experimental part, p. 9875 - 9879 (2011/02/22)
An efficient thiourea promoted MBH reaction of various conjugated nitroalkenes with ethyl glyoxylate was developed. The desired multifunctional products, 2-hydroxy-3-nitro-4-aryl/alkylbut-3-enoate derivatives were obtained in good to high chemical yields
