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Volumn 75, Issue 13, 2010, Pages 4612-4614

Improved synthesis of enantiopure 4-hydroxy[2.2]paracyclophane

Author keywords

[No Author keywords available]

Indexed keywords

[2.2]PARACYCLOPHANE; ENANTIOPURE; SYNTHETIC PROTOCOLS;

EID: 77954122333     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100468s     Document Type: Article
Times cited : (45)

References (46)
  • 5
    • 57649224063 scopus 로고    scopus 로고
    • 1,4-Additions:;;, 1,2-Additions
    • 1,4-Additions: Ay, S.; Nieger, M.; Bräse, S. Chem. - Eur. J. 2008, 14, 11539-11556 1,2-Additions
    • (2008) Chem. - Eur. J. , vol.14 , pp. 11539-11556
    • Ay, S.1    Nieger, M.2    Bräse, S.3
  • 14
    • 0000700630 scopus 로고
    • his pioneering work on paracyclophane chemistry, Cram identified 3 as a byproduct in his attempts to reduce the corresponding diazonium salt with hypophosphoric acid
    • In his pioneering work on paracyclophane chemistry, Cram identified 3 as a byproduct in his attempts to reduce the corresponding diazonium salt with hypophosphoric acid: Cram, D. J.; Allinger, N. L. J. Am. Chem. Soc. 1955, 77, 6289-6294
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 6289-6294
    • Cram, D.J.1    Allinger, N.L.2
  • 25
    • 77954108394 scopus 로고    scopus 로고
    • Results from our laboratories
    • Results from our laboratories.
  • 27
    • 0002737051 scopus 로고    scopus 로고
    • Only indirect resolution methods using enzymes are known. In all cases, 4-acetoxy[2.2]paracyclophane is used as a substrate hydrolyzed via kinetic resolution to enantioenriched 3
    • Only indirect resolution methods using enzymes are known. In all cases, 4-acetoxy[2.2]paracyclophane is used as a substrate hydrolyzed via kinetic resolution to enantioenriched 3: Pamperin, D.; Schulz, C.; Hopf, H.; Syldatk, C.; Pietzsch, M. Eur. J. Org. Chem. 1998, 1441-1445
    • (1998) Eur. J. Org. Chem. , pp. 1441-1445
    • Pamperin, D.1    Schulz, C.2    Hopf, H.3    Syldatk, C.4    Pietzsch, M.5
  • 40
    • 0030602002 scopus 로고    scopus 로고
    • It was also shown that a resolution of the corresponding aldehyde (6) with enantiopure 1-phenyl-2-(4-methylphenyl)ethylamine proceeds in 29% yield over two steps
    • It was also shown that a resolution of the corresponding aldehyde (6) with enantiopure 1-phenyl-2-(4-methylphenyl)ethylamine proceeds in 29% yield over two steps: Banfi, S.; Manfredi, A.; Montanari, F.; Pozzi, G.; Quici, S. J. Mol. Catal. A: Chem. 1996, 113, 77-86
    • (1996) J. Mol. Catal. A: Chem. , vol.113 , pp. 77-86
    • Banfi, S.1    Manfredi, A.2    Montanari, F.3    Pozzi, G.4    Quici, S.5
  • 41
    • 77954091770 scopus 로고    scopus 로고
    • The absolute configuration of the diastereomers of 8 was verified by comparison with literature values (see ref 21)
    • The absolute configuration of the diastereomers of 8 was verified by comparison with literature values (see ref 21).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.