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Volumn 48, Issue 37, 2007, Pages 6471-6474

Rh(I)-catalyzed conjugate addition of alkenylzirconocene chloride: stereoselective formation of carbocycles through cascade reaction

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBONYL DERIVATIVE; ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; KETONE DERIVATIVE; RHENIUM; ZIRCONOCENE;

EID: 34547778378     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.056     Document Type: Article
Times cited : (14)

References (24)
  • 2
    • 34547749794 scopus 로고
    • Trost B.M., and Flemming I. (Eds), Pergamon, Oxford Chapter 1.5
    • Schmaltz H.-G. In: Trost B.M., and Flemming I. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, Oxford Chapter 1.5
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Schmaltz, H.-G.1
  • 7
    • 0037419835 scopus 로고    scopus 로고
    • By the use of organoboronic acid as an organometallic reagent, tandem conjugate addition-aldol cyclization reactions of 2 under Rh(I)-catalyzed conditions have been reported. See, and references cited therein
    • By the use of organoboronic acid as an organometallic reagent, tandem conjugate addition-aldol cyclization reactions of 2 under Rh(I)-catalyzed conditions have been reported. See,. Cauble D.F., Gipson J.D., and Krische M.J. J. Am. Chem. Soc. 125 (2003) 1110 and references cited therein
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 1110
    • Cauble, D.F.1    Gipson, J.D.2    Krische, M.J.3
  • 8
    • 34547816011 scopus 로고    scopus 로고
    • note
    • 2 (4 mL/mmol) at ambient temperature, (ii) concentration of the solution to dryness in vacuo, and addition of the required solvent. We used 1a for most of the examined cases because of its NMR simplicity.
  • 9
    • 34547764202 scopus 로고    scopus 로고
    • note
    • As a side product, 1,2-addition product to ω-aldehyde was obtained in 12% yield.
  • 10
    • 34547773560 scopus 로고    scopus 로고
    • note
    • 2Na: 323.1987. Found: 323.2003.
  • 13
    • 34547750322 scopus 로고    scopus 로고
    • note
    • 4-(R)-BINAP-catalyzed conditions has been reported to give 4 in a high enentioselectivity. See, Ref. 3. In the reaction of 1a with 2a, (S,S)-Chiraphos showed a slight enantioselectivity (20% ee). Other enoyl compounds such as, ester 2c and amide 2d, afforded unsatisfactory results (<20% ee) by the use of other chiral ligands.
  • 15
    • 34547769175 scopus 로고    scopus 로고
    • note
    • Deposited Data-CCDC 651166 contains the supplementary crystallographic data for 7. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.
  • 23
    • 34548543076 scopus 로고    scopus 로고
    • note
    • 2Zn or in the reaction of 3 with cuprate. See, 13a and 13e.
  • 24
    • 34547800610 scopus 로고    scopus 로고
    • note
    • 2: C, 83.46; H, 8.30. Found: C, 83.16; H, 8.24.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.