메뉴 건너뛰기




Volumn 54, Issue 16, 2015, Pages 4768-4772

Rhodium-catalyzed [(3+2)+2] carbocyclization of alkynylidenecyclopropanes with substituted allenes: Stereoselective construction of tri- and tetrasubstituted exocyclic olefins

Author keywords

allenes; cyclizations; olefins; rhodium; synthetic methods

Indexed keywords

CATALYSIS; OLEFINS; RHODIUM; STEREOSELECTIVITY;

EID: 84926512705     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410857     Document Type: Article
Times cited : (45)

References (39)
  • 1
    • 84903496421 scopus 로고    scopus 로고
    • Elsevier, Waltham
    • For recent reviews of cycloaddition and cycloisomerization reactions, see: Comprehensive Organic Synthesis II, Vol. 5 (Eds.:, P. Knochel, G. A. Molander, A. Fürstner,), Elsevier, Waltham, 2014.
    • (2014) Comprehensive Organic Synthesis II , vol.5
    • Knochel, P.1
  • 3
    • 84871576557 scopus 로고    scopus 로고
    • (Eds.: J. G. De Vries, G. A. Molander, P. A. Evans), Thieme, Stuttgart, and references therein
    • C. Aubert, M. Malacria, C. Ollivier, in Science of Synthesis, Vol. 3 (Eds.:, J. G. De Vries, G. A. Molander, P. A. Evans,), Thieme, Stuttgart, 2011, pp. 145-242, and references therein.
    • (2011) Science of Synthesis, Vol. 3 , pp. 145-242
    • Aubert, C.1    Malacria, M.2    Ollivier, C.3
  • 11
    • 53549109323 scopus 로고    scopus 로고
    • Angew. Chem. 2006, 118, 2506-2509
    • (2006) Angew. Chem. , vol.118 , pp. 2506-2509
  • 15
    • 80051958954 scopus 로고    scopus 로고
    • Angew. Chem. 2010, 122, 10082-10086
    • (2010) Angew. Chem. , vol.122 , pp. 10082-10086
  • 18
    • 84876521268 scopus 로고    scopus 로고
    • For a concise total synthesis of the lactarane natural product pyrovellerolactone using the rhodium-catalyzed [(3+2)+2] carbocyclization reaction, see:, P. A. Evans, P. A. Inglesby, K. Kilbride, Org. Lett. 2013, 15, 1798-1801.
    • (2013) Org. Lett. , vol.15 , pp. 1798-1801
    • Evans, P.A.1    Inglesby, P.A.2    Kilbride, K.3
  • 20
    • 18644375951 scopus 로고    scopus 로고
    • For an example of the challenges associated with the rhodium-catalyzed [5+2] cycloaddition of a vinylcyclopropane with substituted allenes, see:, H. A. Wegner, A. de Meijere, P. A. Wender, J. Am. Chem. Soc. 2005, 127, 6530-6531.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 6530-6531
    • Wegner, H.A.1    De Meijere, A.2    Wender, P.A.3
  • 21
    • 84902105381 scopus 로고    scopus 로고
    • For an example of the use of propargylic silanes to circumvent the problems associated with the incorporation of exogenous allenes, see:, P. A. Wender, F. Inagaki, M. Pfaffenbach, M. C. Stevens, Org. Lett. 2014, 16, 2923-2925.
    • (2014) Org. Lett. , vol.16 , pp. 2923-2925
    • Wender, P.A.1    Inagaki, F.2    Pfaffenbach, M.3    Stevens, M.C.4
  • 22
    • 79959999015 scopus 로고    scopus 로고
    • For an example of a rhodium-catalyzed [2+2+2] carbocyclization which favors proximal incorportation of an activated allene, see:, A. T. Brusoe, E. J. Alexanian, Angew. Chem. Int. Ed. 2011, 50, 6596-6600
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 6596-6600
    • Brusoe, A.T.1    Alexanian, E.J.2
  • 23
    • 84862572004 scopus 로고    scopus 로고
    • Angew. Chem. 2011, 123, 6726-6730.
    • (2011) Angew. Chem. , vol.123 , pp. 6726-6730
  • 27
    • 84926458030 scopus 로고    scopus 로고
    • The structure of 3 a was confirmed by X-ray analysis (CCDC 1025060 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.). All other cycloadducts were assigned by analogy using 1H NMR and NOE studies.
  • 29
    • 84926458029 scopus 로고    scopus 로고
    • Angew. Chem. 2014, 126, 4033-4037.
    • (2014) Angew. Chem. , vol.126 , pp. 4033-4037
  • 34
    • 84914154831 scopus 로고    scopus 로고
    • For a recent example which illustrates the challenges with longer tethers in a rhodium-catalyzed [(3+2)+1] carbocyclization, see:, S. Kim, Y. K. Chung, Org. Lett. 2014, 16, 4352-4355.
    • (2014) Org. Lett. , vol.16 , pp. 4352-4355
    • Kim, S.1    Chung, Y.K.2
  • 37
    • 84867051527 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 7430-7434
    • (2012) Angew. Chem. , vol.124 , pp. 7430-7434
  • 39
    • 84898073024 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 10824-10828.
    • (2013) Angew. Chem. , vol.125 , pp. 10824-10828


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.