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Volumn 35, Issue 20, 1994, Pages 3273-3276

Enantiospecific synthesis of 2-amino-3-methyl-4-phosphonobutanoic acids via 14-addition of lithiated Schöllkopf anion to prop-2-enylphosphonates

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3 METHYL 4 PHOSPHONOBUTYRIC ACID; PHOSPHONOAMINO ACID; UNCLASSIFIED DRUG;

EID: 0028240870     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)76883-3     Document Type: Article
Times cited : (22)

References (24)
  • 6
    • 84989444996 scopus 로고
    • Synthesis and Wittig-Horner Reactions of 1-(Functionally)Substituted 2,2-Dimethylpropanephosphonic Esters (1-t-Butyl-substituted Phosphonic Esters)
    • (1983) Synthesis , pp. 449
    • Schanmann1    Fittkau2
  • 12
    • 0025239877 scopus 로고
    • Using excess of 1,2-dibromopropane (6 equivalents) after 14 h reflux 5 as a side product (25%). Both products and unreacted 1,2-dibromopropane could be readily separated by distillation at reduced pressure. This provides a more direct synthesis of β-bromophosphonic esters, than that recently reported
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1833
    • Retherford1    Chou2    Schelkun3    Knochel4
  • 14
    • 0022997891 scopus 로고
    • Asymmetric Synthesis via Heterocyclic Intermediates; XXX1. Asymmetric Synthesis of Glutamic Acids and Derivatives thereof by the Bislactim-Ether Method. Michael-Addition of Methyl 2-Alkenoates to the Lithiated Bislactim-Ether of Cyclo-(L-Val- Gly)
    • (1986) Synthesis , pp. 737
    • Schöllkopf1    Pettig2    Busse3    Egerd4    Dyrbusch5
  • 17
    • 84912905509 scopus 로고    scopus 로고
    • 1H NMR spectra after removal of excess of 2 and side products by flash chromatography.
  • 18
    • 84912922735 scopus 로고    scopus 로고
    • 2O as eluent afforded amino acids 4a,b almost with the solvent front, other impurities being retained.
  • 19
    • 84912917069 scopus 로고    scopus 로고
    • 2O, 90 MHz); 18. [[Truncated]]
  • 20
    • 0000057273 scopus 로고
    • Preparation and Conformational Analysis of Geometric Isomers of 4,5-Dimethyl-2-ethoxy-2-oxo-1,2-oxaphosphorinane and Their 3,3,6,6-Tetradeuterio Analogs.
    • (1972) Acta Chemica Scandinavica , vol.26 , pp. 1794
    • Bergesen1    Vikane2
  • 21
    • 84912934864 scopus 로고    scopus 로고
    • 4 or DIBAL in THF there was no reaction.
  • 22
    • 23044505158 scopus 로고
    • Conformational preferences of the substituents in a six-membered cyclic transition state with a trigonal bipyramidal phosphorus atom may account for these results, as it was reported for the related specific ring opening of cyclic phosphonates by alkoxides. See, for example
    • (1989) Adv. Phys. Org. Chem. , vol.25 , pp. 99
    • Thatcher1    Kluger2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.