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Volumn 78, Issue 4, 2013, Pages 1404-1420

A hetero Diels-Alder approach to the synthesis of chromans (3,4-dihydrobenzopyrans) using oxonium ion chemistry: The oxa-Povarov reaction

Author keywords

[No Author keywords available]

Indexed keywords

[4 + 2] CYCLOADDITION; AROMATIC SUBSTITUTION REACTIONS; CYCLIC ALKENES; DIASTEREO-SELECTIVITY; DIELS-ALDER; IONIC PATHWAYS; LEWIS ACID; METHYLSTYRENE; OXOCARBENIUM; OXONIUM ION; POTENTIAL MECHANISM; PRODUCT DISTRIBUTIONS; SUBSTITUTION PATTERNS;

EID: 84873954350     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302328s     Document Type: Article
Times cited : (39)

References (75)
  • 22
    • 84869417046 scopus 로고    scopus 로고
    • A recent example of the cycloaddition chemistry of vinyl diazoacetates with cationic 2-oxadienes to give chromans has been reported; see: Jadhav, A. M.; Pagar, V. V.; Liu, R.-S. Angew. Chem., Int. Ed. 2012, 51, 11809-11813
    • (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 11809-11813
    • Jadhav, A.M.1    Pagar, V.V.2    Liu, R.-S.3
  • 28
  • 33
  • 45
    • 0003997559 scopus 로고
    • Pergamon Press: London.
    • Coupling constants for 4-substituted flavans have been previously shown to adhere well to the Karplus equation, see: Whalley, W. B. The Chemistry of Flavonoid Compounds; Pergamon Press: London, 1962.
    • (1962) The Chemistry of Flavonoid Compounds
    • Whalley, W.B.1
  • 60
    • 44649126044 scopus 로고    scopus 로고
    • One of the closest mechanistic comparisons to rationalize the relative stereoselectivity (C2/C3) obtained in a stepwise oxa-Povarov reaction is to consider stereoselective Prins reactions between 1,2-disubsituted alkenes and aldehydes RCHO. However, most Prins reactions utilize monosubstituted alkenes and formaldehyde as substrates. One rare example is the iodine-promoted reaction of trans -β-methylstyrene and propanal, which was recently described to give a pure adduct in 88% yield (no dr was reported). The relative stereochemistry of this adduct corresponds to the major diastereomer 18-exo-trans obtained for the oxa-Povarov reaction of trans -β- methylstyrene. See: Yadav, J. S.; Subba Reddy, B. V.; Hara Gopal, A. V.; Narayana Kumar, G. G. K. S.; Madavi, C.; Kunwar, A. C. Tetrahedron Lett. 2008, 49, 4420-4423
    • (2008) Tetrahedron Lett. , vol.49 , pp. 4420-4423
    • Yadav, J.S.1    Subba Reddy, B.V.2    Hara Gopal, A.V.3    Narayana Kumar, G.G.K.S.4    Madavi, C.5    Kunwar, A.C.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.