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Volumn , Issue 7, 2007, Pages 1135-1138

Asymmetric electrophilic fluorination of α-cyanoalkylphosphonates catalyzed by chiral palladium complexes

Author keywords

cyanoalkylphosphonates; fluoroalkylphosphonates; Asymmetric catalysis; Chiral palladium catalysts; Electrophilic fluorination

Indexed keywords

IMIDE; N FLUOROBENZENESULFONIMIDE; ORGANOFLUORINE DERIVATIVE; PALLADIUM COMPLEX; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34248221504     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-977436     Document Type: Article
Times cited : (76)

References (62)
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    • Kim, H.R.1    Kim, D.Y.2
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    • Typical procedure: To a stirred solution of 1-phenyl-1- cyanomethylphosphonate (1a, 12.6 mg, 0.05 mmol, Pd catalyst 4g (3.0 mg, 0.0025 mmol) and 2,6-di-tert-butyl-4-methylpyridine (20.5 mg, 0.1 mmol) in EtOH (0.5 mL) at r.t. was added NFSI (2, 18.9 mg, 0.06 mmol, The reaction mixture was stirred for 12 h at r.t. The mixture was diluted with sat. NH4Cl solution (10 mL) and extracted into EtOAc (3 x 10 mL, The combined organic layers were dried over MgSO4, filtered, concentrated, and purified by flash column chromatography to afford diethyl 1-fluoro-1-phenyl-1-cyanomethylphosphonate 3a (12.2 mg, 90, α]D17 -27.7 (c 0.6, CHCl3, 85% ee, 1H NMR (200 MHz, CDCl3, δ, 1.26-1.38 (m, 6 H, 4.03-4.32 (m, 4 H, 7.42-7.50 (m, 3 H, 7.55-7.67 (m, 2 H, 13C NMR 50 MHz, CDCl3
    • 3):
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    • R = 14.8 (major).
    • R = 14.8 (major).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.