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Volumn 68, Issue 15, 2003, Pages 5819-5825

A multistage, one-pot procedure mediated by a single catalyst: A new approach to the catalytic asymmetric synthesis of β-amino acids

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC PROCEDURES;

EID: 0037697025     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034150e     Document Type: Article
Times cited : (62)

References (53)
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    • note
    • a of Proton Sponge is 12, while that of BQ is not known, but probably similar to that of quinuclidine, which is 11.
  • 31
    • 0038272308 scopus 로고    scopus 로고
    • note
    • The uncatalyzed methanolysis took 48 h at reflux while the catalyzed reaction was complete in 14 h.
  • 33
    • 0037597064 scopus 로고    scopus 로고
    • note
    • N-Benzoyl-α-chloroglycine derivative 2a is easily prepared by the condensation of benzamide with ethyl glyoxlate followed by reaction with oxalyl chloride. See the Supporting Information.
  • 34
    • 0038272283 scopus 로고    scopus 로고
    • note
    • Dry NaH (95%) is utilized in the reaction.
  • 41
    • 0038272282 scopus 로고    scopus 로고
    • note
    • 1H (400 MHz) chemical shifts are given in parts per million (δ) with respect to internal TMS standard.
  • 42
    • 0037597041 scopus 로고    scopus 로고
    • note
    • 3 standard.
  • 43
    • 0038611189 scopus 로고    scopus 로고
    • note
    • 19F NMR using the solid support base piperdine.
  • 53
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    • note
    • The choice of a biphenyl amide protecting group afforded easy deprotection without interfering with other functional groups present in the molecule while maintaining the high yields and selectivities of the asparagine derivatives.


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