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Volumn 47, Issue 20, 2008, Pages 3781-3783

Copper-catalyzed asymmetric propargylic substitution reactions of propargylic acetates with amines

Author keywords

Amination; Asymmetric catalysis; Copper; Nucleophilic substitution; P ligands

Indexed keywords

AMINATION; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; COPPER; COPPER COMPOUNDS; ORGANIC COMPOUNDS; SUBSTITUTION REACTIONS;

EID: 50549097989     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800276     Document Type: Article
Times cited : (185)

References (50)
  • 6
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    • A variety of transition-metal-catalyzed propargylic substitution reactions of propargylic alcohol derivatives with heteroatom-centered nucleophiles have been reported: a J. A. Marshall, M. A. Wolf, J. Org. Chem. 1996, 61, 3238;
    • A variety of transition-metal-catalyzed propargylic substitution reactions of propargylic alcohol derivatives with heteroatom-centered nucleophiles have been reported: a) J. A. Marshall, M. A. Wolf, J. Org. Chem. 1996, 61, 3238;
  • 24
    • 33750167114 scopus 로고    scopus 로고
    • and references therein. For a recent review, see
    • For a recent review, see: L. Zani, C. Bolm, Chem. Commun. 2006, 4263, and references therein.
    • (2006) Chem. Commun , pp. 4263
    • Zani, L.1    Bolm, C.2
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    • For examples, see: a
    • For examples, see: a) C. Wei, C.-J. Li, J. Am. Chem. Soc. 2002, 124, 5638;
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 5638
    • Wei, C.1    Li, C.-J.2
  • 37
    • 53549114563 scopus 로고    scopus 로고
    • Maarseveen and his co-workers
    • presented, June 15, Amsterdam
    • b) Prof. Maarseveen and his co-workers presented a part of the result at the PAC-Symposium 2007 (June 15, 2007, Amsterdam).
    • (2007) a part of the result at the PAC-Symposium
    • Prof1
  • 38
    • 53549126412 scopus 로고    scopus 로고
    • Binap, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl
    • Binap = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl.
  • 39
    • 53549120018 scopus 로고    scopus 로고
    • Biphep, 2,2′-bis(diphenylphosphino)-1,1′-biphenyl
    • Biphep = 2,2′-bis(diphenylphosphino)-1,1′-biphenyl.
  • 40
    • 53549126701 scopus 로고    scopus 로고
    • No reaction occurred in the absence of N,N-diisopropylethylamine. When triethylamine was used in place of N,N-diisopropylethylamine as a base, a similar enantioselectivity was observed.
    • No reaction occurred in the absence of N,N-diisopropylethylamine. When triethylamine was used in place of N,N-diisopropylethylamine as a base, a similar enantioselectivity was observed.
  • 41
    • 53549109218 scopus 로고    scopus 로고
    • (R)-Cl-MeO-biphep=(R)-5,5′-dichloro-6, 6′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-biphenyl, is a commercially available reagent from Strem Chemicals.
    • (R)-Cl-MeO-biphep=(R)-5,5′-dichloro-6, 6′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-biphenyl, is a commercially available reagent from Strem Chemicals.
  • 45
    • 53549100257 scopus 로고    scopus 로고
    • 2, toluene, THF, MeCN, DMF, and 1,4-dioxane.
    • 2, toluene, THF, MeCN, DMF, and 1,4-dioxane.
  • 46
    • 53549097720 scopus 로고    scopus 로고
    • Although a variety of optically active diphosphines and monophosphines, such as Duphos, chiraphos, diop, and mop, were investigated as chiral ligands for the propargylic amination, these did not work effectively. As a result, R-Cl-MeO-biphep was found to be the ligand of choice for the present propargylic amination. The detailed experimental results will be reported in due course
    • Although a variety of optically active diphosphines and monophosphines, such as Duphos, chiraphos, diop, and mop, were investigated as chiral ligands for the propargylic amination, these did not work effectively. As a result, (R)-Cl-MeO-biphep was found to be the ligand of choice for the present propargylic amination. The detailed experimental results will be reported in due course.
  • 49
    • 53549099999 scopus 로고    scopus 로고
    • The molecular structure of a copper-(R)-Cl-MeO-biphep complex has been determined by X-ray crystallography. The detailed experimental results will be reported in due course.
    • The molecular structure of a copper-(R)-Cl-MeO-biphep complex has been determined by X-ray crystallography. The detailed experimental results will be reported in due course.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.