메뉴 건너뛰기




Volumn 63, Issue 18, 1998, Pages 6178-6195

Tandem inter [4 + 2]/intra [3 + 2] cycloadditions of nitroalkenes. Asymmetric synthesis of highly functionalized aminocyclopentanes using the bridged mode (β-tether) process

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CYCLOPENTANE DERIVATIVE;

EID: 0032483565     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9802170     Document Type: Article
Times cited : (39)

References (96)
  • 21
    • 85008270873 scopus 로고
    • Review: (a) Yoshikuni, Y. Trends Glycosci. Glycotechnol. 1991, 1, 184. (b) Winchester, B.; Fleet, G. W. J. Glycobiol. 1992, 2, 199.; Kaushal, G. P.; Elbein, A. D. Trends Glycosci. Glycotechnol. 1993, 3, 184.
    • (1991) Trends Glycosci. Glycotechnol. , vol.1 , pp. 184
    • Yoshikuni, Y.1
  • 22
    • 0026654870 scopus 로고
    • Review: (a) Yoshikuni, Y. Trends Glycosci. Glycotechnol. 1991, 1, 184. (b) Winchester, B.; Fleet, G. W. J. Glycobiol. 1992, 2, 199.; Kaushal, G. P.; Elbein, A. D. Trends Glycosci. Glycotechnol. 1993, 3, 184.
    • (1992) J. Glycobiol. , vol.2 , pp. 199
    • Winchester, B.1    Fleet, G.W.2
  • 23
    • 0343618747 scopus 로고
    • Review: (a) Yoshikuni, Y. Trends Glycosci. Glycotechnol. 1991, 1, 184. (b) Winchester, B.; Fleet, G. W. J. Glycobiol. 1992, 2, 199.; Kaushal, G. P.; Elbein, A. D. Trends Glycosci. Glycotechnol. 1993, 3, 184.
    • (1993) Trends Glycosci. Glycotechnol. , vol.3 , pp. 184
    • Kaushal, G.P.1    Elbein, A.D.2
  • 25
    • 0026567167 scopus 로고
    • For general reviews on the synthesis of carbocyclic nuleosides see: (a) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. b) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
    • (1992) Tetrahedron , vol.48 , pp. 571
    • Borthwick, A.D.1    Biggadike, K.2
  • 28
    • 33947333596 scopus 로고
    • Shealy, Y. F.; Clayton, J. D. J. Am. Chem. Soc. 1966, 88, 3885. Kusaka, T.; Yamamoto, M.; Shibata, M.; Muroi, M.; Kishi, T.; Mizuno, K. J. Antibiot. 1968, 21, 255.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 3885
    • Shealy, Y.F.1    Clayton, J.D.2
  • 50
    • 12044258371 scopus 로고
    • (l) For a recent review on the use of carbohydrate templates for the preparation of carbocycles, see: Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779.
    • (1993) Chem. Rev. , vol.93 , pp. 2779
    • Ferrier, R.J.1    Middleton, S.2
  • 77
    • 7344258692 scopus 로고    scopus 로고
    • 4-promoted cycloaddition, had isomerized to approximately 3/1 (trans/cis) ratio
    • 4-promoted cycloaddition, had isomerized to approximately 3/1 (trans/cis) ratio.
  • 79
    • 7344221866 scopus 로고    scopus 로고
    • Helmchen, G., Huffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart
    • (b) For an excellent discussion of the stereochemical terminology, see: Helmchen, G. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); Edition E21; Helmchen, G., Huffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 1, p 1.
    • (1996) Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); Edition E21 , vol.1 , pp. 1
    • Helmchen, G.1
  • 80
    • 7344246976 scopus 로고    scopus 로고
    • The topicity is defined at the β-carbons of the reactive components
    • The topicity is defined at the β-carbons of the reactive components.
  • 82
    • 7344256605 scopus 로고    scopus 로고
    • note
    • Chiral vinyl ethers, derived from 2,2-diphenylcyclopentanol and TCC, were explored in the [4 + 2] cycloaddition; however, they offered no particular advantage with respect to their preparation, yield, and selectivity.
  • 84
    • 33845374200 scopus 로고
    • For review on nickel boride see: Ganem, B.; Osby, J. O. Chem. Rev. 1986, 86, 763.
    • (1986) Chem. Rev. , vol.86 , pp. 763
    • Ganem, B.1    Osby, J.O.2
  • 85
    • 7344264442 scopus 로고    scopus 로고
    • Determined by chiral stationary phase HPLC, see Supporting Information for details
    • Determined by chiral stationary phase HPLC, see Supporting Information for details.
  • 87
    • 7344241972 scopus 로고    scopus 로고
    • Epimeric ratios ranging from 3.5 to 20/1 have been obtained for this reaction
    • Epimeric ratios ranging from 3.5 to 20/1 have been obtained for this reaction.
  • 88
    • 7344224187 scopus 로고    scopus 로고
    • note
    • 4-promoted cycloaddition had isomerized to an approximately 1.4/1 (cis/trans) ratio.
  • 89
    • 7344249369 scopus 로고    scopus 로고
    • Determined by chiral stationary phase supercritical fluid chromotography (SFC), see Supporting Information for details
    • Determined by chiral stationary phase supercritical fluid chromotography (SFC), see Supporting Information for details.
  • 90
    • 7344254464 scopus 로고    scopus 로고
    • Various solvent and temperatures were tried to optimize the yield and minimize decompostion of this reaction
    • Various solvent and temperatures were tried to optimize the yield and minimize decompostion of this reaction.
  • 91
    • 7344233517 scopus 로고    scopus 로고
    • note
    • A detailed discussion of the [3 + 2] cycloaddition and nitroso acetal stability as well as the mechanism of hydrogenolysis can be found in the preceding paper.
  • 92
    • 7344262777 scopus 로고    scopus 로고
    • The re and si faces are defined at the β-carbon atom of the niroalkene
    • The re and si faces are defined at the β-carbon atom of the niroalkene.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.