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Volumn 1, Issue 23, 2003, Pages 4275-4281

Highly diastereoselective addition of nitromethane anion to chiral α-amidoalkylphenyl sulfones. Synthesis of optically active α-amino acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; AMINO ACIDS; DERIVATIVES; ESTERS; NEGATIVE IONS; OPTICAL PROPERTIES; STEREOCHEMISTRY; SULFUR COMPOUNDS;

EID: 0346349375     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b309211a     Document Type: Article
Times cited : (83)

References (67)
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    • Bloch, R.1
  • 4
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    • (d) R. A. Volkmann, in Comprehensive Organic Synthesis, I. Fleming, B. M. Trost, and S. L. Schreiber, Eds., Pergamon, Oxford, 1991, Vol. 1, pp 355-396.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 355-396
    • Volkmann, R.A.1
  • 27
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    • N-Carbamoylimines can be also prepared by acylation of the corresponding N-silylimines obtained from aromatic aldehydes: (a) R. Kupfer, S. Meier and E.-U. Würthwein, Synthesis, 1984, 688-690
    • (1984) Synthesis , pp. 688-690
    • Kupfer, R.1    Meier, S.2    Würthwein, E.-U.3
  • 44
    • 0346242538 scopus 로고
    • (Windows NT version) Structure Determination Package, Siemens Analytical X-Ray Instruments Inc., Madison, WI
    • Siemens SHELXTLplus Version 5.1 (Windows NT version) Structure Determination Package, Siemens Analytical X-Ray Instruments Inc., Madison, WI, 1988.
    • (1988) Siemens SHELXTLplus Version 5.1
  • 49
    • 0347503376 scopus 로고    scopus 로고
    • Semiempirical PM3 calculations were performed with the Spartan ES 1.0.2, Wavefunction Inc., 18401 Von Karmen Ave., #370, Irvine, CA 92715
    • Semiempirical PM3 calculations were performed with the Spartan ES 1.0.2, Wavefunction Inc., 18401 Von Karmen Ave., #370, Irvine, CA 92715.
  • 62
    • 0000763561 scopus 로고    scopus 로고
    • M. Reetz, Chem. Rev., 1999, 99, 1121-1162.
    • (1999) Chem. Rev. , vol.99 , pp. 1121-1162
    • Reetz, M.1
  • 65
    • 0346872847 scopus 로고    scopus 로고
    • note
    • See electronic supporting information for transition state models leading to compounds 21 and 22†.
  • 67
    • 0348133395 scopus 로고    scopus 로고
    • note
    • As an example, the α-amidoalkylphenyl sulfone obtained from (S)-N-Boc-2-amino-3-phenylpropanal and benzyl carbamate as a 65 : 35 mixture of diastereomers, gives the corresponding nitro derivative in low yield with a similar diastereomeric ratio (60 : 40).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.