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Volumn 127, Issue 27, 2005, Pages 9682-9683

Catalytic, enantioselective, conjugate alkyne addition

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ACID; ALKYNE; COPPER; LIGAND; MELDRUM ACID; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 22144481646     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052411r     Document Type: Article
Times cited : (180)

References (25)
  • 9
    • 4143079275 scopus 로고    scopus 로고
    • Conjugate addition reactions of terminal acetylenes using late transition metal catalysts (Rh, Ru, Pd) have been documented. However, these reactions are limited to β-unsubstituted vinyl ketones or acrylates. See: (a) Lerum, R. V.; Chisholm, J. D. Tetrahedron Lett. 2004, 45, 6591-6594.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 6591-6594
    • Lerum, R.V.1    Chisholm, J.D.2
  • 11
    • 9144270060 scopus 로고    scopus 로고
    • and references therein
    • (c) Chen, L.; Li, C.-J. Chem. Commun. 2004, 20, 2362-2364 and references therein.
    • (2004) Chem. Commun. , vol.20 , pp. 2362-2364
    • Chen, L.1    Li, C.-J.2
  • 16
    • 22144473432 scopus 로고    scopus 로고
    • note
    • For ligand structures and names, see Supporting Information.
  • 18
    • 22144488905 scopus 로고    scopus 로고
    • note
    • The relative configuration of the ligand 7 was unambiguously established by X-ray crystallographic analysis (ref 18).
  • 19
    • 22144467819 scopus 로고    scopus 로고
    • note
    • The absolute configuration of the ascorbate has no effect on the asymmetric induction; in the addition to 1a using (+)-ascorbate, 7 and ent-7 furnished enantiomeric products of identical % ee.
  • 20
    • 22144498206 scopus 로고    scopus 로고
    • note
    • We found that a 2:1 ligand/copper ratio led to complete inhibition of the reaction.
  • 21
    • 22144492009 scopus 로고    scopus 로고
    • CCDC 268029 (4-bromoanilide of 2b) and CCDC 268030 (7) contain the supplementary crystallographic data for this communication. These data can be obtained online free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html (or from Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21 EZ, U.K.; Fax (+44) 1223-336-033; or deposit@cccd.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.