메뉴 건너뛰기




Volumn , Issue 1, 2004, Pages 98-106

Stereoselective synthesis of 1,2,3-trisubstituted 1,3-dienes through novel [3,3]-sigmatropic rearrangements in α-allenic methanesulfonates: Application to the preparation of fused tricyclic systems by tandem rearrangement/Diels-Alder reaction

Author keywords

Allenes; Cycloaddition; Dienes; Domino reactions; Sigmatropic rearrangement

Indexed keywords

1,3 DIENE DERIVATIVE; ALKADIENE; ALLENE DERIVATIVE; ALPHA ALLENIC METHANESULFONATE; MESYLIC ACID DERIVATIVE; METHANESULFONYL CHLORIDE; TERTIARY AMINE; UNCLASSIFIED DRUG;

EID: 11844305031     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400527     Document Type: Article
Times cited : (40)

References (50)
  • 3
    • 84985633316 scopus 로고
    • [1b] S. J. Danishefsky, M. P. DeNinno, Angew. Chem. Int. Ed. Engl. 1987, 26, 15; Angew. Chem. 1987, 99, 24.
    • (1987) Angew. Chem. , vol.99 , pp. 24
  • 8
    • 0038249079 scopus 로고    scopus 로고
    • [3b] B. M. Trost, C. Jonasson, Angew. Chem. Int. Ed. 2003, 42, 2063; Angew. Chem. 2003, 115, 2109. A related intermediate was also postulated by Yu: C.-M. Yu, Y.-M. Kim, J.-M. Kim, Synlett 2003, 1518.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 2063
    • Trost, B.M.1    Jonasson, C.2
  • 9
    • 1542292777 scopus 로고    scopus 로고
    • [3b] B. M. Trost, C. Jonasson, Angew. Chem. Int. Ed. 2003, 42, 2063; Angew. Chem. 2003, 115, 2109. A related intermediate was also postulated by Yu: C.-M. Yu, Y.-M. Kim, J.-M. Kim, Synlett 2003, 1518.
    • (2003) Angew. Chem. , vol.115 , pp. 2109
  • 10
    • 0042069797 scopus 로고    scopus 로고
    • [3b] B. M. Trost, C. Jonasson, Angew. Chem. Int. Ed. 2003, 42, 2063; Angew. Chem. 2003, 115, 2109. A related intermediate was also postulated by Yu: C.-M. Yu, Y.-M. Kim, J.-M. Kim, Synlett 2003, 1518.
    • (2003) Synlett , pp. 1518
    • Yu, C.-M.1    Kim, Y.-M.2    Kim, J.-M.3
  • 17
    • 11844293833 scopus 로고    scopus 로고
    • note
    • Trisubstituted carbon-carbon double bonds are present in a diverse set of organic molecules and the development of new methods for their synthesis remains an ongoing challenge in synthetic organic chemistry.
  • 19
    • 0038000454 scopus 로고    scopus 로고
    • It has been reported that allenic N-tosyl-2-oxazolidinones can undergo 1,3-sulfonyl migration to afford unisolated azadiene intermediates. [6b] H. Horino, M. Kimura, S. Tanaka, T. Okajima, Y. Tamaru, Chem. Eur. J. 2003, 9, 2419.
    • (2003) Chem. Eur. J. , vol.9 , pp. 2419
    • Horino, H.1    Kimura, M.2    Tanaka, S.3    Okajima, T.4    Tamaru, Y.5
  • 20
    • 0042262416 scopus 로고    scopus 로고
    • There is literature precedence for the 1,3-shift of sulfonyl groups in γ,γ-difluorinated allylic sulfonates: [6c] T. Yamazaki, S. Hiraoka, J. Sakamoto, T. Kitazume, Org. Lett. 2001, 3, 743.
    • (2001) Org. Lett. , vol.3 , pp. 743
    • Yamazaki, T.1    Hiraoka, S.2    Sakamoto, J.3    Kitazume, T.4
  • 21
    • 11844249722 scopus 로고    scopus 로고
    • note
    • It has been proposed that reactions between propargyl bromides and metals generate equilibria between allenyl and propargyl organometallics. This metallotropic rearrangement often results in poor regioselection in the final organic product, because both organometallic species can react with the carbonyl compound.
  • 22
    • 11844291738 scopus 로고    scopus 로고
    • note
    • α-Allenol anti-(+)-2a was obtained as a very minor component from indium-mediated Barbier-type coupling between 1-bromo-2-butyne and 4-oxoazetidine-2-carbaldehyde (+)-1a.
  • 23
    • 2442708813 scopus 로고    scopus 로고
    • For the preparation of 3-aryl-1,3-dienes through Suzuki reaction of α-allenols, see: [9a] M. Yoshida, T. Gotou, M. Ihara, Chem. Commun. 2004, 1124.
    • (2004) Chem. Commun. , pp. 1124
    • Yoshida, M.1    Gotou, T.2    Ihara, M.3
  • 24
    • 0037068114 scopus 로고    scopus 로고
    • N2′-type addition-elimination reactions of 1-aryl-2,3-allenols, see: [9b] S. Ma, G. Wang, Tetrahedron Lett. 2002, 43, 5723.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 5723
    • Ma, S.1    Wang, G.2
  • 25
    • 0035977212 scopus 로고    scopus 로고
    • For the palladium-catalyzed preparation of 3-bromo-1,3-dienes from acetylated α-allenols, see: [9c] A. Horvath, J.-E. Bäckvall, J. Org. Chem. 2001, 66, 8120.
    • (2001) J. Org. Chem. , vol.66 , pp. 8120
    • Horvath, A.1    Bäckvall, J.-E.2
  • 27
    • 33750173220 scopus 로고
    • For selected reviews, see: [10a] L. F. Tietze, U. Beifuss, Angew. Chem. Int. Ed. Engl. 1993, 32, 131; Angew. Chem. 1993, 105, 137.
    • (1993) Angew. Chem. , vol.105 , pp. 137
  • 29
    • 0001847186 scopus 로고    scopus 로고
    • (Eds.: M. Shibasaki, J. F. Stoddart, F. Vögtle), Wiley-VCH, Weinheim
    • [10c] L. F. Tietze, F. Haunert, in Stimulating Concepts in Chemistry, (Eds.: M. Shibasaki, J. F. Stoddart, F. Vögtle), Wiley-VCH, Weinheim, 2000, p. 39-64.
    • (2000) Stimulating Concepts in Chemistry , pp. 39-64
    • Tietze, L.F.1    Haunert, F.2
  • 33
    • 0002979399 scopus 로고    scopus 로고
    • For selected reviews, see: [11a] K. C. Nicolau, D. Vourloumis, N. Winssiger, P. Baran, Angew. Chem. Int. Ed. 2000, 39, 44; Angew. Chem. 2000, 112, 46.
    • (2000) Angew. Chem. , vol.112 , pp. 46
  • 37
    • 0035813893 scopus 로고    scopus 로고
    • [12b] M. Nörret, M. S. Sherburn, Angew. Chem. Int. Ed. 2001, 40, 4074; Angew. Chem. 2001, 113, 4198.
    • (2001) Angew. Chem. , vol.113 , pp. 4198
  • 39
    • 0000368861 scopus 로고    scopus 로고
    • [12c] K. C. Nicolau, J. Li, Angew. Chem. Int. Ed. 2001, 40, 4264; Angew. Chem. 2001, 113, 4394.
    • (2001) Angew. Chem. , vol.113 , pp. 4394
  • 50
    • 11844257375 scopus 로고    scopus 로고
    • note
    • Full spectroscopic and analytical data for compounds not included in this Exp. Sect. are described in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.