메뉴 건너뛰기




Volumn 50, Issue 10, 2011, Pages 2354-2358

Access to high levels of molecular complexity by one-pot iridium/enamine asymmetric catalysis

Author keywords

Asymmetric catalysis; Iridium; Isomerization; One pot reactions; Organocatalysis

Indexed keywords

ALLYLIC ALCOHOL; ASYMMETRIC CATALYSIS; CATALYTIC SEQUENCES; CHEMICAL EQUATIONS; ELECTROPHILES; ENANTIOSELECTIVE; FUNCTIONALIZATIONS; IRIDIUM CATALYST; MOLECULAR COMPLEXITY; ONE POT; ONE-POT REACTION; ORGANOCATALYSIS; TEAM SPIRIT;

EID: 79952053373     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201007001     Document Type: Article
Times cited : (111)

References (84)
  • 1
    • 70349943846 scopus 로고    scopus 로고
    • For recent reviews, see
    • For recent reviews, see: a) Z. Shao, H. Zhang, Chem. Soc. Rev. 2009, 38, 2745;
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 2745
    • Shao, Z.1    Zhang, H.2
  • 3
    • 36849014339 scopus 로고    scopus 로고
    • For recent examples of transition-metal/enamine asymmetric catalysis, see
    • For recent examples of transition-metal/enamine asymmetric catalysis, see: a) F. Bihelovic, R. Matovic, B. Vulovic, R. N. Saicic, Org. Lett. 2007, 9, 5063;
    • (2007) Org. Lett. , vol.9 , pp. 5063
    • Bihelovic, F.1    Matovic, R.2    Vulovic, B.3    Saicic, R.N.4
  • 22
    • 69249088448 scopus 로고    scopus 로고
    • For selected reviews on enamine catalysis, see
    • For selected reviews on enamine catalysis, see: a) S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178;
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 2178
    • Bertelsen, S.1    Jørgensen, K.A.2
  • 42
    • 2142754143 scopus 로고
    • Allylic alcohols with tetrasubstituted olefins are much less reactive. Furthermore, a substituent on C2 implies that the tautomerization is the enantiodetermining step. If the metal is not involved, or if background tautomerization is substantially faster, the racemic product is obtained. For a relevant discussion, see
    • Allylic alcohols with tetrasubstituted olefins are much less reactive. Furthermore, a substituent on C2 implies that the tautomerization is the enantiodetermining step. If the metal is not involved, or if background tautomerization is substantially faster, the racemic product is obtained. For a relevant discussion, see: S. Bergens, B. Bosnich, J. Am. Chem. Soc. 1991, 113, 958.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 958
    • Bergens, S.1    Bosnich, B.2
  • 47
    • 26444568120 scopus 로고    scopus 로고
    • For the specific use of sulfone 4, see
    • For the specific use of sulfone 4, see: a) S. Mossé, A. Alexakis, Org. Lett. 2005, 7, 4361;
    • (2005) Org. Lett. , vol.7 , pp. 4361
    • Mossé, S.1    Alexakis, A.2
  • 56
    • 79952063292 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for details.
  • 69
    • 79952059694 scopus 로고    scopus 로고
    • note
    • When N-chlorosuccinimide or N-fluorodi(benzenesulfonyl)- amine (0.5 equiv) was used as a source of electrophilic chloride or fluoride, 5 was obtained in a 1.3:1.0 or 1.2:1.0 syn/anti diastereoisomeric ratio, respectively, along with aldehyde 6 in nearly racemic form. These observations suggest that in the present system, C-C bond formation, rather than enamine formation, is both the rate- and enantiodetermining step. For a relevant discussion, see reference [13].
  • 70
    • 73349089534 scopus 로고    scopus 로고
    • 3 substituent has a larger Charton value (n) than a tBu group (1.40 versus 1.24). For recent discussions on the use of Charton values in the context of asymmetric catalysis, see
    • 3 substituent has a larger Charton value (n) than a tBu group (1.40 versus 1.24). For recent discussions on the use of Charton values in the context of asymmetric catalysis, see: a) J. J. Miller, M. S. Sigman, Angew. Chem. 2008, 120, 783;
    • (2008) Angew. Chem. , vol.120 , pp. 783
    • Miller, J.J.1    Sigman, M.S.2
  • 84
    • 79952063679 scopus 로고    scopus 로고
    • note
    • Preliminary attempts to carry out the catalytic reactions in a tandem rather than sequential manner were successful with the achiral catalyst 1a but not with the chiral catalyst 1b. These studies are ongoing.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.