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Organic Letters
Volumn 9, Issue 4, 2007, Pages 683-685
Asymmetric syntheses of 1-Aryl-2,2,2-trifluoroethylamines via diastereoselective 1,2-addition of arylmetals to 2-Methyl-N-(2,2,2- trifluoroethylidene)propane-2-sulfinamide
Author keywords

[No Author keywords available]
Indexed keywords

2 METHYL N (2,2,2 TRIFLUOROETHYLIDENE)PROPANE 2 SULFINAMIDE; 2-METHYL-N-(2,2,2-TRIFLUOROETHYLIDENE)PROPANE-2-SULFINAMIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ETHYLAMINE; FLUORINATED HYDROCARBON; IMINE; ORGANOMETALLIC COMPOUND; SULFONIUM DERIVATIVE; UNCLASSIFIED DRUG;
EID: 33847796729     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol063001q     Document Type: Article
Times cited : (50)
References (30)
  • 23
    • 0000574262 scopus 로고    scopus 로고
    • 19F NMR spectrometry. The stereochemistry of 3 was assigned as E based on NOE between the proton of inline and the proton of tert-butyl and by analogy (see Davis, F. A.; Reddy, R. E.; Szewczyk, G.; Reddy, V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555-2563 and ref 5e).
    • 19F NMR spectrometry. The stereochemistry of 3 was assigned as E based on NOE between the proton of inline and the proton of tert-butyl and by analogy (see Davis, F. A.; Reddy, R. E.; Szewczyk, G.; Reddy, V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555-2563 and ref 5e).
  • 29
    • 33847793144 scopus 로고    scopus 로고
    • Experimental Procedure for 5a. To a solution of N-tert-butane-sulfinamide (S)-1 (200 mg, 1.65 mmol) in toluene (3.3 mL) were added trifluoroacetaldehyde hydrate 2a (75% in aqueous solution, 200 μL, 1.82 mmol) and molecular sieves pellets 4 Å (1 g) from Acros. The reaction mixture was stirred at 40°C for 6 h under nitrogen to provide the crude imine 3. A solution of bromobenzene (530 μL, 4.95 mmol) in THF (3.3 mL) in a flame-dried round-bottom flask under nitrogen was cooled to -78 °C, and a solution of n-BuLi (2.5 M in hexanes, 1.65 mL, 4.13 mmol) was added dropwise. The reaction mixture was aged at -78 °C for 1 h. The crude imine 3 was cooled to -78 °C and transferred via cannula to the reaction mixture. The resulting mixture was aged at -78 °C for 5 min and transferred to a cooled (0 °C) saturated aqueous NH4Cl. The aqueous layer was extracted three times with ethyl acetate. The organic extracts were co
    • 4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using ethyl acetate-hexanes (25:75) to afford 5a in 66% yield (302 mg).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.