Synthesis of functionalized enamines: A facile and efficient protocol toward N-protected α,β-dehydroamino acid derivatives

Synlett

Volumn , Issue 6, 2008, Pages 861-866

  Sun, Yun ^a   Wang, Xiaozhao ^a,b   Zheng, Xiufang ^a   Zhao, Kang ^a  

^a TIANJIN UNIVERSITY   (China)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

, dehydroamino acid derivatives; Electron withdrawing group; Elimination; Functionalized enamines; Substitution

Indexed keywords

ALPHA BETA DEHYDROAMINO ACID DERIVATIVE; ALPHA BROMOKETONE; AMINO ACID DERIVATIVE; BROMIDE; ENAMINE; HYDROXAMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ISOMERIZATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 42149152144     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042901     Document Type: Article

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25. 3 chromatography or silica gel chromatography to afford the desired products 4a-u.
26. 3 (2.2 mmol) in anhyd MeCN (20 mL) was added α-bromoketone 1h (2.4 mmol) in one portion under stirring at 40°C. When the starting material 2a had disappeared, DBU (2.0 mmol) was added dropwise and the temperature was raised to reflux. When the intermediate 3v was not detected via TLC analysis any more, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography to afford the desired products 4v.
27. 13C NMR, and NOE spectra were recorded on a Varian Inova 500 MHz instrument. High-resolution electrospray ionization mass spectra (HR-ESI-MS) were obtained using an IonSpec Ultima 7.0T FTICR ESI mass spectrometer.
28. 3, Z = 2; CCDC 672176.
29. +: 401.1836; found: 401.1836.