메뉴 건너뛰기




Volumn 52, Issue 42, 2013, Pages 11114-11118

A powerful hydrogen-bond-donating organocatalyst for the enantioselective intramolecular oxa-michael reaction of α,β-unsaturated amides and esters

Author keywords

asymmetric synthesis; heterocycles; hydrogen bonding; Michael reaction; stereoselective catalysis

Indexed keywords

ASYMMETRIC SYNTHESIS; ENANTIOSELECTIVE; HETEROCYCLES; MICHAEL REACTIONS; NATURAL PRODUCTS; ORGANOCATALYSTS; STEREOSELECTIVE CATALYSIS; UNSATURATED AMIDES;

EID: 84885454399     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201305492     Document Type: Article
Times cited : (104)

References (79)
  • 2
    • 0036373830 scopus 로고    scopus 로고
    • for recent examples of biologically active isoxazoline and isoxazolidines, see
    • S. Kanemasa, Synlett 2002, 1371; for recent examples of biologically active isoxazoline and isoxazolidines, see
    • (2002) Synlett , pp. 1371
    • Kanemasa, S.1
  • 5
    • 33947646506 scopus 로고    scopus 로고
    • (Eds.: Ø. M. Andersen, K. R. Markham), Taylor & Francis, London
    • Flavonoids: Chemistry, Biochemistry and Applications (Eds.:, Ø. M. Andersen, K. R. Markham,), Taylor & Francis, London, 2006
    • (2006) Flavonoids: Chemistry, Biochemistry and Applications
  • 15
    • 79957698619 scopus 로고    scopus 로고
    • It has been estimated that as much as 25 % of all synthetic pharmaceutical drugs contain an amide moiety; see
    • It has been estimated that as much as 25 % of all synthetic pharmaceutical drugs contain an amide moiety; see:, S. D. Roughley, A. M. Jordan, J. Med. Chem. 2011, 54, 3451.
    • (2011) J. Med. Chem. , vol.54 , pp. 3451
    • Roughley, S.D.1    Jordan, A.M.2
  • 19
    • 79959895362 scopus 로고    scopus 로고
    • for selected recent enantioselective intermolecular oxa-Michael reactions, see
    • E. Hartmann, D. J. Vyas, M. Oestreich, Chem. Commun. 2011, 47, 7917; for selected recent enantioselective intermolecular oxa-Michael reactions, see
    • (2011) Chem. Commun. , vol.47 , pp. 7917
    • Hartmann, E.1    Vyas, D.J.2    Oestreich, M.3
  • 46
    • 84858694556 scopus 로고    scopus 로고
    • Diastereoselective intramolecular oxa-Michael reactions of α,β-unsaturated imides and N-acyl pyrroles have been reported, see:, and references cited therein
    • Diastereoselective intramolecular oxa-Michael reactions of α,β-unsaturated imides and N-acyl pyrroles have been reported, see:, H. Fuwa, N. Ichinokawa, K. Noto, M. Sasaki, J. Org. Chem. 2012, 77, 2588, and references cited therein.
    • (2012) J. Org. Chem. , vol.77 , pp. 2588
    • Fuwa, H.1    Ichinokawa, N.2    Noto, K.3    Sasaki, M.4
  • 52
    • 2942635094 scopus 로고    scopus 로고
    • For a discussion on the reactivity of α,β-unsaturated ester surrogates, see:, and references cited therein
    • For a discussion on the reactivity of α,β-unsaturated ester surrogates, see:, S. Matsunaga, T. Kinoshita, S. Okada, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 7559, and references cited therein.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 7559
    • Matsunaga, S.1    Kinoshita, T.2    Okada, S.3    Harada, S.4    Shibasaki, M.5
  • 54
    • 34447136276 scopus 로고    scopus 로고
    • for selected examples of enantioselective Michael additions of carbon nucleophiles to α,β-unsaturated N-acyl pyrroles, see
    • M. P. Sibi, K. Itoh, J. Am. Chem. Soc. 2007, 129, 8064; for selected examples of enantioselective Michael additions of carbon nucleophiles to α,β-unsaturated N-acyl pyrroles, see
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 8064
    • Sibi, M.P.1    Itoh, K.2
  • 64
    • 77951758941 scopus 로고    scopus 로고
    • for selected recent examples, see
    • Y. Takemoto, Chem. Pharm. Bull. 2010, 58, 593; for selected recent examples, see
    • (2010) Chem. Pharm. Bull. , vol.58 , pp. 593
    • Takemoto, Y.1
  • 72
    • 0038637120 scopus 로고    scopus 로고
    • for a recent example of a Cu-catalyzed intermolecular oxa-Michael reaction to acrylamides, see
    • I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 8696; for a recent example of a Cu-catalyzed intermolecular oxa-Michael reaction to acrylamides, see
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 8696
    • Stewart, I.C.1    Bergman, R.G.2    Toste, F.D.3
  • 77
    • 84874951130 scopus 로고    scopus 로고
    • For a recent elegant synthesis, see:, and references cited therein
    • For a recent elegant synthesis, see:, Y. Kawato, S. Chaudhary, N. Kumagai, M. Shibasaki, Chem. Eur. J. 2013, 19, 3802, and references cited therein.
    • (2013) Chem. Eur. J. , vol.19 , pp. 3802
    • Kawato, Y.1    Chaudhary, S.2    Kumagai, N.3    Shibasaki, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.