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Volumn 74, Issue 20, 2009, Pages 7603-7607

Enantioselective ring-opening reactions of racemic ethynyl epoxides via copper-allenylidene intermediates: Efficient approach to chiral β-amino alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALLENYLIDENE COMPLEXES; ALLENYLIDENES; AMINO ALCOHOLS; BIOLOGICALLY ACTIVE COMPOUNDS; CHEMICAL EQUATIONS; CHIRAL LIGAND; ENANTIOSELECTIVE; ETHYNYL; HIGH YIELD; NATURAL PRODUCTS; OPTICALLY ACTIVE; RING OPENING REACTION; SYNTHETIC APPROACH;

EID: 70349847238     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901064n     Document Type: Article
Times cited : (96)

References (34)
  • 16
    • 70349878426 scopus 로고    scopus 로고
    • BIPHEP = 2,2′-Bis(diphenylphosphino)-1,1′-biphenyl
    • BIPHEP = 2,2′-Bis(diphenylphosphino)-1,1′-biphenyl.
  • 17
    • 49349113140 scopus 로고    scopus 로고
    • 2 was added in the catalytic ring-opening reaction. We consider that an equivalent amount of diphosphine is used to reduce Cu(II) complex to the active species Cu(I) complex
    • 2 was added in the catalytic ring-opening reaction. We consider that an equivalent amount of diphosphine is used to reduce Cu(II) complex to the active species Cu(I) complex: Nieto, S.; Metola, P.; Lynch, V. M.; Anslyn, E. V. Organometallics 2008, 27, 3608.
    • (2008) Organometallics , vol.27 , pp. 3608
    • Nieto, S.1    Metola, P.2    Lynch, V.M.3    Anslyn, E.V.4
  • 18
    • 15944401743 scopus 로고    scopus 로고
    • Cu(II)-catalyzed reactions of epoxides with carbonyl compounds such as acetone gave the corresponding 1,3-dioxolanes
    • (b) Cu(II)-catalyzed reactions of epoxides with carbonyl compounds such as acetone gave the corresponding 1,3-dioxolanes: Krasik, P.; Bohemier-Bernard, M.; Yu, Q. Synlett 2005, 854.
    • (2005) Synlett , pp. 854
    • Krasik, P.1    Bohemier-Bernard, M.2    Yu, Q.3
  • 19
    • 70349883722 scopus 로고    scopus 로고
    • 2 promoted the ring-opening reaction more smoothly under the same reaction conditions
    • 2 promoted the ring-opening reaction more smoothly under the same reaction conditions.
  • 21
    • 0033920416 scopus 로고    scopus 로고
    • N2 type of ring-opening reactions of racemic epoxides with nucleophiles, see: (a)
    • N2 type of ring-opening reactions of racemic epoxides with nucleophiles, see: (a) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 421
    • Jacobsen, E.N.1
  • 23
    • 7444231089 scopus 로고    scopus 로고
    • N2 type of ring-opening reactions of optically active epoxides with nucleophiles, see: (c)
    • N2 type of ring-opening reactions of optically active epoxides with nucleophiles, see: (c) Taber, D. F.; He, Y.; Xu, M. J. Am. Chem. Soc. 2004, 126, 13900.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13900
    • Taber, D.F.1    He, Y.2    Xu, M.3
  • 25
    • 70349883724 scopus 로고    scopus 로고
    • note
    • We will report more detailed results in due course. Hattori, G.; Matsuzawa, H.; Sakata, K.; Miyake, Y.; Nishibayashi, Y. Unpublished results.
  • 26
    • 70349857744 scopus 로고    scopus 로고
    • note
    • The X-ray analysis of a major enantiomer of the tosylated compound of 2f indicates that the absolute configuration of 2f is R. The molecular structure of the tosylated compound of 2f was confirmed by X-ray analysis. See the Supporting Information for experimental details.
  • 27
    • 0028238209 scopus 로고
    • Murahashi and his co-workers proposed a free copper allenylidene as an intermediate in the copper-catalyzed propargylic amination of propargylic esters with amines. However, no experimental evidence of this intermediate appeared
    • Murahashi and his co-workers proposed a free copper allenylidene as an intermediate in the copper-catalyzed propargylic amination of propargylic esters with amines. However, no experimental evidence of this intermediate appeared: Imada, Y.; Yuasa, M.; Nakamura, I.; Murahashi, S.-I. J. Org. Chem. 1994, 59, 2282.
    • (1994) J. Org. Chem. , vol.59 , pp. 2282
    • Imada, Y.1    Yuasa, M.2    Nakamura, I.3    Murahashi, S.-I.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.