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Volumn 43, Issue 10, 2004, Pages 1235-1238

Enantioselective H-atom transfer reactions: A new methodology for the synthesis of β2-amino acids

Author keywords

Amino acids; Asymmetric catalysis; Enantioselective H atom transfer; Lewis acids; Radical reactions

Indexed keywords

ACTIVATION ANALYSIS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 2642518615     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353000     Document Type: Article
Times cited : (77)

References (51)
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    • note
    • 2. The details of these experiments will be reported in a separate full account.
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    • note
    • Several ligand-Lewis acid combinations were also evaluated. Of these, magnesium salts with ligand 9a gave the best results.
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    • note
    • 3SiH; TMS = trimethylsilyl), tributyltin hydride gave the addition products most efficiently (clean with very few byproducts) and with the highest enantioselectivity.
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    • note
    • The catalytic loading was varied from 10 to 100 mol %. The enantioselectivity remained nearly constant (ca. 80% ee) for loadings between 20 and 75 mol %.
  • 46
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    • note
    • The higher enantioselectivities observed for 8a and 8f at 30 mol % catalytic loading are not an experimental artifact. Further experimentation is required to identify the origin(s) of this anomaly.
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    • P. E. Coffey, K. Drauz, S. M. Roberts, J. Skidmore, J. A. Smith, Chem. Commun. 2001, 2330. See also ref. [3e]. Product 7a also has the S configuration (see the Supporting Information). By analogy, we assume that the face selectivity is the same for the other substrates.
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    • note
    • This model is similar to that proposed by Metzger and coworkers in their work on diastereoselective H-atom transfer reactions with methylene glutarates (see ref. [7a]).
  • 49
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    • note
    • At the present time we do not have a clear picture of the influence of the chiral ligand on the rotamer geometry of the ester substituent and its impact on the observed enantioselectivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.