메뉴 건너뛰기




Volumn 52, Issue 19, 2013, Pages 5046-5051

Cu-catalyzed chemoselective preparation of 2-(pinacolato)boron-substituted allylcopper complexes and their insitu site-, diastereo-, and enantioselective additions to aldehydes and ketones

Author keywords

aldol products; allylations; copper; enantioselective catalysis; vinylborons

Indexed keywords

ALDOL PRODUCTS; ALLYLATIONS; ENANTIOSELECTIVE; ENANTIOSELECTIVE ADDITION; ENANTIOSELECTIVE CATALYSIS; FUNCTIONALIZATIONS; THREE-COMPONENT; VINYLBORONS;

EID: 84875138892     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201301018     Document Type: Article
Times cited : (164)

References (37)
  • 1
    • 70349156384 scopus 로고    scopus 로고
    • For a review on multicomponent catalytic reactions, see:, B. B. Touré, D. G. Hall, Chem. Rev. 2009, 109, 4439.
    • (2009) Chem. Rev. , vol.109 , pp. 4439
    • Touré, B.B.1    Hall, D.G.2
  • 3
    • 70349947984 scopus 로고    scopus 로고
    • 2-Substituted allylmetal species cannot be accessed by Ir- and Ru-catalyzed reductive couplings with allenes, and there are no related processes involving ketones
    • Angew. Chem. Int. Ed. 2009, 48, 34. 2-Substituted allylmetal species cannot be accessed by Ir- and Ru-catalyzed reductive couplings with allenes, and there are no related processes involving ketones.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 34
  • 8
    • 84862155975 scopus 로고    scopus 로고
    • 1 (vs. π-allyl) complexes, based on computational studies and a report regarding the electronically related allylzinc systems by Okuda. See
    • 1 (vs. π-allyl) complexes, based on computational studies and a report regarding the electronically related allylzinc systems by Okuda. See:, C. Lichtenberg, J. Engel, T. P. Spaniol, U. Englert, G. Raabe, J. Okuda, J. Am. Chem. Soc. 2012, 134, 9805.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 9805
    • Lichtenberg, C.1    Engel, J.2    Spaniol, T.P.3    Englert, U.4    Raabe, G.5    Okuda, J.6
  • 11
    • 46249097084 scopus 로고    scopus 로고
    • For an overview of (largely Pd-catalyzed) three-component coupling reactions with allenes, affording reagents that can be used in allyl addition processes, see:, M. Jeganmohan, C.-H. Cheng, Chem. Commun. 2008, 3101.
    • (2008) Chem. Commun. , pp. 3101
    • Jeganmohan, M.1    Cheng, C.-H.2
  • 14
    • 31544464044 scopus 로고    scopus 로고
    • For direct Ti-catalyzed aldol addition involving ketones and aryl aldehydes, see:, R. Mahrwald, B. Schetter, Org. Lett. 2006, 8, 281.
    • (2006) Org. Lett. , vol.8 , pp. 281
    • Mahrwald, R.1    Schetter, B.2
  • 15
    • 84877707173 scopus 로고    scopus 로고
    • 2 is slower via σ-bond metathesis and must proceed by alkoxide-assisted ligand exchange (versus 16mol % base needed with an aldehyde), see
    • 2 is slower via σ-bond metathesis and must proceed by alkoxide-assisted ligand exchange (versus 16mol % base needed with an aldehyde), see:, F. Gao, J. L. Carr, A. H. Hoveyda, Angew. Chem. 2012, 124, 6717
    • (2012) Angew. Chem. , vol.124 , pp. 6717
    • Gao, F.1    Carr, J.L.2    Hoveyda, A.H.3
  • 17
    • 73249139284 scopus 로고    scopus 로고
    • Further Cu-B additions to the vinylboron products do not occur, see
    • Further Cu-B additions to the vinylboron products do not occur, see:, Y. Lee, H. Jang, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 18234.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 18234
    • Lee, Y.1    Jang, H.2    Hoveyda, A.H.3
  • 28
    • 84863828459 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 7263; for reactions of ketones and stoichiometric amounts of allylboronic acids (not 2-B substituted), isolated from allylic alcohols by a Pd-catalyzed process, see
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 7263
  • 30
    • 84871954230 scopus 로고    scopus 로고
    • See the Supporting Information for additional references
    • Angew. Chem. Int. Ed. 2012, 51, 13050. See the Supporting Information for additional references.
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 13050
  • 36
    • 38049151296 scopus 로고    scopus 로고
    • Reactions with aliphatic aldehydes are scarce (none with enals); one reported example requires >140h; see
    • S. Aratake, T. Itoh, T. Okano, N. Nagae, T. Sumiya, M. Shoji, Y. Hayashi, Chem. Eur. J. 2007, 13, 10246. Reactions with aliphatic aldehydes are scarce (none with enals); one reported example requires >140h; see
    • (2007) Chem. Eur. J. , vol.13 , pp. 10246
    • Aratake, S.1    Itoh, T.2    Okano, T.3    Nagae, N.4    Sumiya, T.5    Shoji, M.6    Hayashi, Y.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.