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Volumn 126, Issue 24, 2004, Pages 7559-7570

Catalytic asymmetric 1,4-addition reactions using α,β- unsaturated N-acylpyrroles as highly reactive monodentate α,β- unsaturated ester surrogates

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ORGANIC ACIDS; OXIDATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 2942635094     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0485917     Document Type: Article
Times cited : (156)

References (99)
  • 1
    • 0035126119 scopus 로고    scopus 로고
    • For recent review for catalytic asymmetric 1,4-addition reaction, see: (a) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
    • (2001) Synthesis , pp. 171
    • Krause, N.1    Hoffmann-Röder, A.2
  • 3
    • 2942638311 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin; Chapter 31
    • (c) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Chapter 31.
    • (1999) Comprehensive Asymmetric Catalysis
  • 6
    • 0034817259 scopus 로고    scopus 로고
    • For selected recent examples using oxazolidinone and pyrrolidinone as achiral template in catalytic asymmetric 1,4-addition reactions, see: (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4480
    • Evans, D.A.1    Scheidt, K.A.2    Johnston, J.N.3    Willis, M.C.4
  • 26
    • 2942692368 scopus 로고    scopus 로고
    • note
    • For imides as substrate, both monodentate and bidentate transition states were proposed, depending on the catalyst and reaction. See ref 6c and e.
  • 27
    • 2942666479 scopus 로고    scopus 로고
    • note
    • 2Zn to bidentate substrates with chiral metal catalysts. Appropriate tuning of chiral ligands was necessary. For representative recent examples of catalytic asymmetric 1,4-addition of organozinc reagents, see ref 1a and 2g and references therein.
  • 37
    • 0001304728 scopus 로고    scopus 로고
    • (b) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Adv. Synth. Catal. 2002, 344, 3. Both enantiomers of linked-BINOL are also commercially available from Wako Pure Chemical Industries, Ltd. Catalog No. for (S,S)-5 is No. 152-02431 and (R,R)-5, No. 155-02421.
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 3
    • Matsunaga, S.1    Ohshima, T.2    Shibasaki, M.3
  • 40
    • 0033606864 scopus 로고    scopus 로고
    • Application to catalytic asymmetric reactions: (a) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595.
    • (1999) Org. Lett. , vol.1 , pp. 595
    • Evans, D.A.1    Johnson, D.S.2
  • 48
    • 2942631585 scopus 로고    scopus 로고
    • note
    • Although Arai et al. reported the utility of α,β-unsaturated N-acyt-2-substituted-pyrrole as a Michael acceptor, it might not function as a monodentate substrate because of the coordinating functional group at 2-position. See ref 14e and f.
  • 49
    • 0141618331 scopus 로고    scopus 로고
    • and references therein
    • Ekkati, A. R.; Bates, D. K. Synthesis 2003, 1959 and references therein. The scope of the reaction was limited to aromatic amides and cinnamamide.
    • (2003) Synthesis , pp. 1959
    • Ekkati, A.R.1    Bates, D.K.2
  • 51
    • 2942668666 scopus 로고    scopus 로고
    • note
    • Synthesis and application of carbonyldipyrrole 8 was reported by Evans et al. See ref 15a.
  • 55
  • 69
    • 2942694565 scopus 로고    scopus 로고
    • note
    • 3/BINOL complex. Catalyst concentration should be kept low (<5-10 mM) to achieve the best enantioselectivity, because undesired dimeric and oligomeric species would increase under concentrated conditions. See ref 10b for mechanistic studies.
  • 70
    • 2942651167 scopus 로고    scopus 로고
    • note
    • 3 was purchased from Kojundo Chemical Laboratory Co., Ltd. (Fax: +81-492-84-1351. sales@kojundo.co.jp).
  • 71
    • 2942677450 scopus 로고    scopus 로고
    • note
    • Reaction time for imidazolide: with 10 mol % of La-BINOL catalyst, at room temperature, 3.5 h, 86% yield and 5 mol % of La-BINOL catalyst, at room temperature, 12 h, 73% yield. Reaction time for amide: 5-10 mol % Sm-BINOL catalyst, at room temperature, 3-24 h, >90% yield. See refs 23 and 24.
  • 72
    • 2942677451 scopus 로고    scopus 로고
    • note
    • With imidazolide or amide as substrate, 5-10 mol % catalyst loading was essential for completion of the reaction.
  • 74
    • 2942668665 scopus 로고    scopus 로고
    • note
    • With less reactive CMHP as oxidant, acid imidazolide resulted in low chemical yield (18 h, 47% yield with 10 mol % catalyst). See ref 23.
  • 75
    • 2942690186 scopus 로고    scopus 로고
    • note
    • 8-BINOL catalyst was used, although the reaction did not proceed well with 1 mol % catalyst loading in the case of N-acylimidazole as substrate (section E, Scheme 4).
  • 76
    • 2942679713 scopus 로고    scopus 로고
    • note
    • 3 ([Sm-cat] = 0.3 mM), epoxide was obtained in less than 10% yield.
  • 77
    • 2942662293 scopus 로고    scopus 로고
    • note
    • 2-urea with base, mCPBA, and aqNaClO with phase-transfer catalyst, either resulted in decompositions of enone or afforded product in low yield (<20%).
  • 90
    • 2942642711 scopus 로고    scopus 로고
    • note
    • 2 substituted phenyl ketone was 77/23. See ref 9a.
  • 91
    • 0000189651 scopus 로고
    • LUMO energy was calculated using the B3LYP method with 6-31G* as basis sets. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648
    • Becke, A.D.1
  • 94
    • 2942655627 scopus 로고    scopus 로고
    • note
    • In addition to the adverse effects of the liberated 4-phenylimidazole, product inhibition by epoxy peroxy ester is also postulated to explain the low reactivity with 1 mol % catalyst (Scheme 4b). Epoxy peroxy ester 21 would function as a bidentate ligand toward the Sm catalyst. Adverse effects of the bidentate coordination were also observed when using an α,β- unsaturated Weinreb amide as a substrate. See ref 24c.
  • 95
    • 2942694566 scopus 로고    scopus 로고
    • note
    • For the conversion of N-acylpyrrole unit, see refs 13 and 15 and references therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.