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Volumn 31, Issue 45, 1990, Pages 6461-6464

The asymmetric synthesis of α-chloro α-alkyl and α-methyl α-alkyl phosphonic acids of high enantiomeric purity.

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

EID: 0025000351     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)97091-6     Document Type: Article
Times cited : (89)

References (15)
  • 8
    • 0025348425 scopus 로고
    • Stereoselective alkylations of chiral phosphorus, stabilized benzylic carbanions lead to α-alkylated α-benzyl phosphonic acids of high enantiomeric purity, Prof. S. E. Denmark, private communication. For an elegant study of the structure of such carbanions, see
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 864
    • Denmark1    Dorow2
  • 11
    • 84918130593 scopus 로고    scopus 로고
    • In a typical procedure, a solution of LDA (1.55 mmoles) in dry THF is cooled at −100°C and treated with 1 (0.333 g, 1.41 mmoles) in 4.5 mL of dry THF at −100°C. After 15 min., propyl iodide (0.360 g, 2.11 mmoles) is added. After l0 min., the mixture is quenched at −100°C with excess MeOH then warmed to room temp.. Usual work up and chromatography affords 0.326 g (83%yield) of the α-alkylated product (Table 1, Entry 3).
  • 15
    • 84918130592 scopus 로고    scopus 로고
    • 31P, NMR, IR and HRMS.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.