메뉴 건너뛰기




Volumn 50, Issue 6, 2011, Pages 1410-1414

Highly enantioselective synthesis of α-amino acid derivatives by an NHC-catalyzed intermolecular stetter reaction

Author keywords

amino acids; asymmetric catalysis; N heterocyclic carbene; organocatalysis; protonation

Indexed keywords

AMINO ACID DERIVATIVES; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ACCEPTORS; N-HETEROCYCLIC CARBENE; N-HETEROCYCLIC CARBENES; ORGANOCATALYSIS; STEREOSELECTIVE PROTONATION; STETTER REACTION;

EID: 79551655842     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006548     Document Type: Article
Times cited : (193)

References (90)
  • 1
    • 79551656215 scopus 로고    scopus 로고
    • For reviews on the stereoselective synthesis of α-amino acids, see
    • For reviews on the stereoselective synthesis of α-amino acids, see
  • 5
    • 79551673225 scopus 로고    scopus 로고
    • NHC-catalyzed asymmetric protonations
    • NHC-catalyzed asymmetric protonations
  • 7
    • 43049110636 scopus 로고    scopus 로고
    • for a very recent example of an NHC-catalyzed intramolecular, moderately diastereoselective protonation, see
    • B. E. Maki, A. Chan, K. A. Scheidt, Synthesis 2008, 1306; for a very recent example of an NHC-catalyzed intramolecular, moderately diastereoselective protonation, see
    • (2008) Synthesis , pp. 1306
    • Maki, B.E.1    Chan, A.2    Scheidt, K.A.3
  • 10
    • 79551656894 scopus 로고    scopus 로고
    • For organocatalyzed tandem conjugate addition and asymmetric protonations, see
    • For organocatalyzed tandem conjugate addition and asymmetric protonations, see
  • 20
    • 79551671582 scopus 로고    scopus 로고
    • For metal-catalyzed tandem conjugate addition and asymmetric protonations, see
    • For metal-catalyzed tandem conjugate addition and asymmetric protonations, see
  • 29
    • 79551662489 scopus 로고    scopus 로고
    • For metal-catalyzed tandem conjugate addition and asymmetric protonations leading to the asymmetric synthesis of α-amino acid derivatives, see
    • For metal-catalyzed tandem conjugate addition and asymmetric protonations leading to the asymmetric synthesis of α-amino acid derivatives, see
  • 32
    • 1042279654 scopus 로고    scopus 로고
    • hydrogen atom transfer
    • Angew. Chem. Int. Ed. 2004, 43, 719; hydrogen atom transfer
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 719
  • 36
    • 79551673512 scopus 로고    scopus 로고
    • For reviews on NHC organocatalysis, see
    • For reviews on NHC organocatalysis, see
  • 42
    • 77950197170 scopus 로고    scopus 로고
    • for a recent review on the physicochemical properties of NHCs, see
    • J. L. Moore, T. Rovis, Top. Curr. Chem. 2010, 291, 77; for a recent review on the physicochemical properties of NHCs, see
    • (2010) Top. Curr. Chem. , vol.291 , pp. 77
    • Moore, J.L.1    Rovis, T.2
  • 45
    • 79551678899 scopus 로고    scopus 로고
    • For seminal work, see
    • For seminal work, see
  • 49
    • 84982348671 scopus 로고
    • for reviews, see
    • Angew. Chem. Int. Ed. Engl. 1974, 13, 539; for reviews, see
    • (1974) Angew. Chem. Int. Ed. Engl. , vol.13 , pp. 539
  • 53
    • 79551673933 scopus 로고    scopus 로고
    • For pioneering studies, see
    • For pioneering studies, see
  • 65
    • 79251581914 scopus 로고    scopus 로고
    • For the highly selective, although low-yielding enzyme-catalyzed intermolecular Stetter reaction, see
    • For the highly selective, although low-yielding enzyme-catalyzed intermolecular Stetter reaction, see, C. Dresen, M. Richter, M. Pohl, S. Lüdeke, M. Müller, Angew. Chem. 2010, 122, 6750
    • (2010) Angew. Chem. , vol.122 , pp. 6750
    • Dresen, C.1    Richter, M.2    Pohl, M.3    Lüdeke, S.4    Müller, M.5
  • 72
    • 79551676544 scopus 로고    scopus 로고
    • note
    • -10 mol % base and 15 mol % NHCâHCl 3 were used and stirred in toluene for 30 min before addition of the starting materials to ensure that there is no free base.
  • 73
    • 79551664771 scopus 로고    scopus 로고
    • See the Supporting Information for details.
    • See the Supporting Information for details.
  • 74
    • 79551658645 scopus 로고    scopus 로고
    • note
    • [17]
  • 76
    • 3142640259 scopus 로고
    • For a truly pioneering report, see.
    • For a truly pioneering report, see, R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 3719
    • Breslow, R.1
  • 77
    • 1942437578 scopus 로고    scopus 로고
    • for additional insightful mechanistic studies of the Stetter reaction, see
    • T. Dudding, K. N. Houk, Proc. Natl. Acad. Sci. USA 2004, 101, 5770; for additional insightful mechanistic studies of the Stetter reaction, see
    • (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 5770
    • Dudding, T.1    Houk, K.N.2
  • 80
    • 79551655791 scopus 로고    scopus 로고
    • For NHC-catalyzed hydroacylation reactions of unactivated alkenes, alkynes, and arynes that might proceed by a related concerted transition state, see
    • For NHC-catalyzed hydroacylation reactions of unactivated alkenes, alkynes, and arynes that might proceed by a related concerted transition state, see
  • 84
    • 78650118285 scopus 로고    scopus 로고
    • for a related work, see
    • Angew. Chem. Int. Ed. 2010, 49, 9761; for a related work, see
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 9761
  • 86
    • 79551670631 scopus 로고    scopus 로고
    • For analogous concerted transformations proceeding through five-membered transition states, see
    • For analogous concerted transformations proceeding through five-membered transition states, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.