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Volumn 10, Issue 46, 2012, Pages 9287-9294

Chiral picolylamines for Michael and aldol reactions: Probing substrate boundaries

Author keywords

[No Author keywords available]

Indexed keywords

ACID ADDITIVES; ALDOL REACTIONS; AROMATIC ALDEHYDE; BIFUNCTIONAL CATALYSIS; CHIRAL DIAMINE; CYCLOHEXANONES; CYCLOPENTANONE; ENAMINES; ISOBUTYRALDEHYDE; MICHAEL ADDITIONS; NEW PRODUCT; NITROSTYRENE; ORGANOCATALYSTS;

EID: 84868645016     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob26382c     Document Type: Article
Times cited : (34)

References (94)
  • 13
    • 0035891780 scopus 로고    scopus 로고
    • For a very early example of acetone and cyclohexanone addition to aromatic aldehydes, see
    • J. M. Betancort C. F. Barbas III Org. Lett. 2001 3 3737 3740
    • (2001) Org. Lett. , vol.3 , pp. 3737-3740
    • Betancort, J.M.1    Barbas Iii, C.F.2
  • 14
    • 0037037912 scopus 로고    scopus 로고
    • Ley's early report also provided inspiration for other researchers, see
    • M. Nakadai S. Saito H. Yamamoto Tetrahedron 2002 58 8167 8177
    • (2002) Tetrahedron , vol.58 , pp. 8167-8177
    • Nakadai, M.1    Saito, S.2    Yamamoto, H.3
  • 40
    • 77955958653 scopus 로고    scopus 로고
    • For a 2-picolylamine based pyrrolidine catalyst (aldol reaction), see structure 2a within
    • T. C. Nugent M. N. Umar A. Bibi Org. Biomol. Chem. 2010 8 4085 4089
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 4085-4089
    • Nugent, T.C.1    Umar, M.N.2    Bibi, A.3
  • 41
  • 42
    • 0036927410 scopus 로고    scopus 로고
    • For 1,3- and 1,4-pyrrolidine-pyridines, for cyclic ketone and aldehyde additions to β-nitrostyrene, see ref. 9h For a 2,6-bis(pyrrolidine- triazole) substituted pyridine Michael catalyst (cyclohexanone additions to β-nitrostyrene derivatives), see
    • A. Córdova W. Notz C. F. Barbas III Chem. Commun. 2002 3024 3025
    • (2002) Chem. Commun. , pp. 3024-3025
    • Córdova, A.1    Notz, W.2    Barbas Iii, C.F.3
  • 50
    • 0000935673 scopus 로고    scopus 로고
    • Other reports exist in which similar effects have been previously reported. For example, see
    • D. M. Spero S. R. Kapadia J. Org. Chem. 1997 62 5537 5541
    • (1997) J. Org. Chem. , vol.62 , pp. 5537-5541
    • Spero, D.M.1    Kapadia, S.R.2
  • 56
    • 84876091704 scopus 로고    scopus 로고
    • The following superior results were reported for product (Table 3): Zhao (10 mol% catalyst loading, 3:1 cyclopentanone/β-nitrostyrene, 80% yield, 90:10 dr, 98% ee), Xu (20 mol% catalyst loading, 2:1 cyclopentanone/β- nitrostyrene, 88% yield, 83:17 dr, 95% ee), and Chandrasekhar (10 mol% catalyst loading, 5:1 cyclopentanone/β-nitrostyrene, 97% yield, 97:3 dr, 90% ee). Respectively see ref. 8a,d,f. Correspondence with Professor Chandrasekhar enabled confirmation of the cited data in this footnote For examples of primary amine based catalysts for aldol reactions, see
    • S. H. Xue-jing Zhang S.-p. Liu X.-m. Li M. Yan A. S. C. Chan Chem. Commun. 2009 833 835
    • (2009) Chem. Commun. , vol.4 , pp. 833-835
    • Xue-Jing, S.H.1    Zhang, S.-P.2    Liu, X.-M.3    Li, M.4    Yan, A.S.C.5
  • 91
    • 82055208588 scopus 로고    scopus 로고
    • The anti stereochemistry assigned to 9b and 9c is assumed based on those reported for 9a and 9b, see for example: ref. 30 and 31
    • G. Ma A. Bartoszewicz I. Ibrahem A. Córdova Adv. Synth. Catal. 2011 353 3114 3122
    • (2011) Adv. Synth. Catal. , vol.353 , pp. 3114-3122
    • Ma, G.1    Bartoszewicz, A.2    Ibrahem, I.3    Córdova, A.4
  • 93
    • 0038106171 scopus 로고    scopus 로고
    • The bifunctional catalysis model has been previously summarized, specifically see pages 3124-3125 of
    • R. Bloch Chem. Rev. 1998 98 1407 1438
    • (1998) Chem. Rev. , vol.98 , pp. 1407-1438
    • Bloch, R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.