메뉴 건너뛰기




Volumn 131, Issue 35, 2009, Pages 12576-12578

Improved dienophilicity of nitrocycloalkenes: Prospects for the development of a trans-Diels-Alder paradigm

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CYCLOADDUCTS; DIELS-ALDER; STEREO-SELECTIVE;

EID: 69849115865     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9058926     Document Type: Article
Times cited : (38)

References (38)
  • 14
    • 33947450396 scopus 로고
    • The possibility of epimerizing a cis junction, obtained from a Diels-Alder reaction, to the trans series was well recognized and practiced by Woodward and co-workers in their total synthesis of steroids. Other instances of epimerization are also cited herein. (a)
    • The possibility of epimerizing a cis junction, obtained from a Diels-Alder reaction, to the trans series was well recognized and practiced by Woodward and co-workers in their total synthesis of steroids. Other instances of epimerization are also cited herein. (a) Woodward, R. B.; Sondheimer, F.; Taub, D.; Heusler, K.; McLamore, W. M. J. Am. Chem. Soc. 1952, 74, 4223-4251.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 4223-4251
    • Woodward, R.B.1    Sondheimer, F.2    Taub, D.3    Heusler, K.4    McLamore, W.M.5
  • 16
    • 0024524867 scopus 로고
    • Of course, this approach requires a vicinal keto group to enable epimerization and the capacity to apply strict thermodynamic or kinetic controls to govern the junction stereochemistry
    • (c) Mukhopadhyay, A.; Ali, S. M.; Husain, M.; Suryawanshi, S. N.; Bhakuni, D. S. Tetrahedron Lett. 1989, 30, 1853-1856. Of course, this approach requires a vicinal keto group to enable epimerization and the capacity to apply strict thermodynamic or kinetic controls to govern the junction stereochemistry.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 1853-1856
    • Mukhopadhyay, A.1    Ali, S.M.2    Husain, M.3    Suryawanshi, S.N.4    Bhakuni, D.S.5
  • 18
    • 0003527998 scopus 로고    scopus 로고
    • Wiley-VCH: New York, and pertinent references cited therein
    • Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001 and pertinent references cited therein.
    • (2001) The Nitro Group in Organic Synthesis
    • Ono, N.1
  • 26
    • 69849107267 scopus 로고    scopus 로고
    • note
    • Following completion of this work, we noted that in footnote 18 in ref 10, Professor Corey futuristically envisioned potential value of reductive denitration at the junction. However no results are provided. Nonetheless the kernel of the idea can be found in Corey's comment.
  • 29
    • 69849090850 scopus 로고    scopus 로고
    • note
    • Cycloaddition of compound 3 with several 2-silyloxy-1,3-butadienes as well as diene 8 in toluene under the variety of conditions did not proceed at all.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.