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Volumn 2, Issue 24, 2000, Pages 3937-3940

Intramolecular Diels-Alder Reaction by Self-assembly of the Components on a Lewis Acid Template

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EID: 0000447319     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0067235     Document Type: Article
Times cited : (65)

References (73)
  • 2
    • 0000048482 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • Reviews: (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 513-550.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 513-550
    • Roush, W.R.1
  • 11
    • 0001646244 scopus 로고
    • Recent examples of Mg, Zn, B, and Al based tethers: (a) Stork, G.; Chan, T. Y. J. Am. Chem. Soc. 1995, 117, 6595-6596.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6595-6596
    • Stork, G.1    Chan, T.Y.2
  • 18
    • 85037507792 scopus 로고    scopus 로고
    • note
    • Adducts from reactions of 2H-thiopyrans with dienophiles are, after desulfurization, synthetically equivalent to adducts from cis-dienes.
  • 53
    • 85037515044 scopus 로고    scopus 로고
    • note
    • The dienes are acid sensitive and are consumed by dimerization and/or polymerization in these cases.
  • 55
    • 37049137296 scopus 로고
    • Addition of MeMgBr (1 equiv) to a toluene solution of 1a gave a clear solution only with a MeMgBr/1a ratio near 0.5; with greater or lesser amounts of MeMgBr, the mixture was cloudy. With a total ROH:MeMgBr ratio of 2, the use of pentanol (1 equiv) as a "dummy" alcohol gave a faster and more efficient reaction. Presumably, the ROH:ROMgBr ratio affects the speciation of ROMgBr. For an example of a dimeric structure, see: Moseley, P. T.; Shearer, H. M. M. J. Chem. Soc., Chem. Commun. 1968, 279-280. Reaction is much slower with MeMgCl and faster but less efficient with MeMgI.
    • (1968) J. Chem. Soc., Chem. Commun. , pp. 279-280
    • Moseley, P.T.1    Shearer, H.M.M.2
  • 56
    • 85037504896 scopus 로고    scopus 로고
    • note
    • The regioselectivity is the ratio of ([5] + [6]):([3] + [4] + [7]).
  • 57
    • 85037492463 scopus 로고    scopus 로고
    • note
    • A predominance of 5/6 regioisoniers is expected on the basis of greater electron-donating properties of a methyl group vs a hydroxymethyl or methoxymethyl group. Only 3/4/7 regioisomers can form if diene and dienophile are tethered by association with a Lewis acid in the TS.
  • 59
    • 85037512499 scopus 로고    scopus 로고
    • note
    • For example, 1a was 1.2 times more reactive than 1b toward 2a in toluene solution at 120°C as determined in a competition experiment.
  • 60
    • 85037495188 scopus 로고    scopus 로고
    • note
    • Chelation of 8 by 2b (i.e. 15b) prevents IMDA reaction; IMDA reaction is feasible with monodentate coordination (e.g., 14).
  • 62
    • 85037518548 scopus 로고    scopus 로고
    • note
    • 1H NMR of the crude reaction mixture; yields were determined using an internal standard.
  • 63
    • 85037517282 scopus 로고    scopus 로고
    • note
    • 2AlCl-mediated competition reactions which were faster though less reproducible.
  • 65
    • 85037503475 scopus 로고    scopus 로고
    • Diene 1b did not react under these conditions
    • Diene 1b did not react under these conditions.
  • 67
    • 85037507514 scopus 로고    scopus 로고
    • The C-Me configuration of 22 was not rigorously determined
    • The C-Me configuration of 22 was not rigorously determined.
  • 68
    • 85037496810 scopus 로고    scopus 로고
    • The preparation and reactions of thiopyran dienes will be described separately
    • The preparation and reactions of thiopyran dienes will be described separately.
  • 69
    • 0030908679 scopus 로고    scopus 로고
    • For similar Mg(II)-mediated [3 + 2] cycloadditions of nitrile oxides with allylic alcohols, see: (a) Kanemasa, S.; Hidetoshi, Y.; Shinsuke, K. Tetrahedron Lett. 1997, 38, 4095-4098.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4095-4098
    • Kanemasa, S.1    Hidetoshi, Y.2    Shinsuke, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.