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Volumn , Issue 28, 2005, Pages 3586-3588

Acyclic amino acid-catalyzed direct asymmetric aldol reactions: Alanine, the simplest stereoselective organocatalyst

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; ALANINE TETRAZOLE 3; ALDEHYDE; AMINO ACID DERIVATIVE; ASPARTIC ACID; ISOLEUCINE; KETONE; SERINE; UNCLASSIFIED DRUG; VALINE;

EID: 23944447473     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b507968n     Document Type: Article
Times cited : (258)

References (58)
  • 3
    • 0003417469 scopus 로고    scopus 로고
    • B. M. Trost, I. Fleming, C.-H. Heathcock, Eds.; Pergamon, Oxford, For examples of application in total synthesis see:
    • Comprehensive Organic Synthesis, Vol. 2,, B. M. Trost, I. Fleming, C.-H. Heathcock,, Eds.; Pergamon, Oxford
    • Comprehensive Organic Synthesis, Vol. 2
  • 23
    • 0037043180 scopus 로고    scopus 로고
    • For the proline-catalyzed intermolecular aldol reaction see:
    • B. List Tetrahedron 58 5573
    • Tetrahedron , vol.58 , pp. 5573
    • List, B.1
  • 52
    • 0030621130 scopus 로고    scopus 로고
    • For examples of the use of dihydroxyacetone mimetic 2a in proline-catalyzed reactions see:
    • J. R. Cronin S. Pizzarello Science 275 951
    • Science , vol.275 , pp. 951
    • Cronin, J.R.1    Pizzarello, S.2
  • 54
    • 17244373834 scopus 로고    scopus 로고
    • Performing the l-alanine-catalyzed reaction without addition of water enabled the isolation of 2a in 55% yield with 2 : 1 dr and > 99% ee after 20 days The stereochemical outcome of the acyclic l-amino acid-catalyzed asymmetric aldol reactions between ketones and aldehydes was the same as when l-proline was used as the catalyst, see:
    • I. Ibrahem A. Córdova Tetrahedron Lett. 46 3363
    • Tetrahedron Lett. , vol.46 , pp. 3363
    • Ibrahem, I.1    Córdova, A.2
  • 55
    • 0037425534 scopus 로고    scopus 로고
    • This beneficial effect of water has also been observed in proline and its derivatives-catalyzed aldol reactions. See: reference 12b and
    • L. Hoang S. Bahmanyar K. N. Houk B. List J. Am. Chem. Soc. 125 16
    • J. Am. Chem. Soc. , vol.125 , pp. 16
    • Hoang, L.1    Bahmanyar, S.2    Houk, K.N.3    List, B.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.