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Volumn 77, Issue 10, 2012, Pages 4711-4724

Diastereoselective reductive nitro-Mannich reactions

Author keywords

[No Author keywords available]

Indexed keywords

ACYL MIGRATION; DIASTEREOMERIC RATIOS; DIASTEREOSELECTIVE; NITRO-MANNICH REACTION; NITROALKENES; NITROAMINES; REPRESENTATIVE SELECTION;

EID: 84862092292     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300535h     Document Type: Article
Times cited : (19)

References (57)
  • 13
    • 0346339657 scopus 로고    scopus 로고
    • For a recent review, see
    • For a recent review, see: Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017
    • (2004) Tetrahedron , vol.60 , pp. 1017
    • Ballini, R.1    Petrini, M.2
  • 42
    • 33947437707 scopus 로고
    • 3N-catalyzed Henry reaction (;), followed by dehydration using MsCl and DIPEA (Melton, J. McMurry, J. E. J. Org. Chem. 1975, 40, 2138).
    • 3N-catalyzed Henry reaction (Fieser, L. F.; Gates, M. J. Am. Chem. Soc. 1946, 68, 2249), followed by dehydration using MsCl and DIPEA (Melton, J.; McMurry, J. E. J. Org. Chem. 1975, 40, 2138).
    • (1946) J. Am. Chem. Soc. , vol.68 , pp. 2249
    • Fieser, L.F.1    Gates, M.2
  • 46
    • 12344317934 scopus 로고    scopus 로고
    • 1H NMR chemical shifts (δ) and coupling constants (J) recorded for the protons adjacent to the two nitrogen atoms. In our nitro-Mannich system, the vast majority of products have given anti selectivity, for which we have forwarded a transition state model. See refs 5a and 8b and
    • 1H NMR chemical shifts (δ) and coupling constants (J) recorded for the protons adjacent to the two nitrogen atoms. In our nitro-Mannich system, the vast majority of products have given anti selectivity, for which we have forwarded a transition state model. See refs 5a and 8b and: Anderson, J. C.; Howell, G. P. J. Org. Chem. 2005, 70, 549-555
    • (2005) J. Org. Chem. , vol.70 , pp. 549-555
    • Anderson, J.C.1    Howell, G.P.2
  • 47
    • 84862113983 scopus 로고
    • U.S. Patent 4,322,53
    • 2] was formed from the oxidation of DIPEA by TFAA (for precedent see: Schreiber, S. L. U.S. Patent 4,322,537, 1982). PMP amines are less basic, so the weaker pyridine base could be used, which gave a cleaner and more efficient reaction.
    • (1982)
    • Schreiber, S.L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.