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Volumn 120, Issue 4, 1998, Pages 657-663

Highly regio- and enantioselective catalytic hydrogenation of enamides in conjugated diene systems: Synthesis and application of γ,δ-unsaturated amino acids

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; AMINO ACID; BULGECININE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

EID: 0032481423     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9731074     Document Type: Article
Times cited : (133)

References (71)
  • 29
    • 0002260975 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York, Chapter 2
    • (a) Halpern, J. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 2.
    • (1985) Asymmetric Synthesis , vol.5
    • Halpern, J.1
  • 41
    • 0012359665 scopus 로고
    • For a review see Maercker, A. Org. React. 1965, 14, 335-344.
    • (1965) Org. React. , vol.14 , pp. 335-344
    • Maercker, A.1
  • 43
    • 2642666993 scopus 로고    scopus 로고
    • Configurations of all the starting materials and products of the coupling reactions were proven by NMR including NOE and NOESY experiments
    • Configurations of all the starting materials and products of the coupling reactions were proven by NMR including NOE and NOESY experiments.
  • 44
    • 2642594604 scopus 로고    scopus 로고
    • Minor enantiomer not detected by GC analysis
    • Minor enantiomer not detected by GC analysis.
  • 53
    • 2642694213 scopus 로고    scopus 로고
    • A 25 m Chrompack Chirasil-L-Val column was used for determinations of enantiomeric excesses
    • A 25 m Chrompack Chirasil-L-Val column was used for determinations of enantiomeric excesses.
  • 56
    • 2642628240 scopus 로고    scopus 로고
    • note
    • As the distal double bond of 2 was reduced, the enantiomeric excess of the monoreduced material (2) decreased showing moderate reverse substrate selectivity for the overreduction reaction (i.e., the major enantiomer of 2 was preferentially reduced causing the % ee of the monoreduced material to decrease). When the overreduction reaction was allowed to go to completion, the % ee of the resulting fully reduced material was identical with the initial % ee of 2.
  • 68
    • 2642660982 scopus 로고    scopus 로고
    • note
    • 3, hexanes). (Equation Presented)
  • 69
    • 2642693226 scopus 로고    scopus 로고
    • note
    • f = 2.15 kcal/mol for the two diastereomers.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.