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Volumn 63, Issue 49, 2007, Pages 12149-12159

Dimethylaluminum methide complex Tf2CHAlMe2: an effective catalyst for Diels-Alder reaction of α,β-unsaturated lactone derivatives with cyclopentadiene

Author keywords

, Unsaturated lactones; Bis(trifluoromethanesulfonyl)methane; Diels Alder reaction; Lewis acid

Indexed keywords

ALPHA,BETA UNSATURATED LACTONE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; DELTA METHYLLACTONE DERIVATIVE; DIMETHYLALUMINUMMETHIDE COMPLEX; EPSILON METHYLLACTONE DERIVATIVE; GAMMA LACTONE DERIVATIVE; GAMMA METHYLLACTONE DERIVATIVE; LACTONE DERIVATIVE; LEWIS ACID; UNCLASSIFIED DRUG;

EID: 35348971920     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.061     Document Type: Article
Times cited : (21)

References (73)
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    • note
    • 2 with liberation of 2 mol of methane gas.
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    • 7a Jonas and co-workers also reported a rapid equilibrium of bis-silylated triflic amide between N,N-bis-silylated form and N,O-bis-silylated form:
    • 7a Jonas and co-workers also reported a rapid equilibrium of bis-silylated triflic amide between N,N-bis-silylated form and N,O-bis-silylated form:. Jonas S., Westerhausen M., and Simchen G. J. Organomet. Chem. 548 (1997) 131-137
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    • 3Al.
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    • note
    • The present Lewis acid systems were not effective for the DA reaction of 3a with acyclic dienes, e.g., isoprene and 2,3-dimethyl-1,3-butadiene.
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    • note
    • *)-2-hydroxypropyl]bicyclo-[2.2.1]hept-5-ene-2-carboxamide for endo-cis-3g], 658581 (endo-cis-3h), and 658583 (endo-trans-3h). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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    • note
    • In this paper, endo-cis isomers mean endo adducts having relative cis-relationship between angular hydrogen and pendant methyl group on lactone structure; endo-trans isomers mean the endo adducts having trans-relationship between angular hydrogen and pendant methyl group.
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    • note
    • 3Al' at 60 °C, respectively. According to the results, retro DA reaction and the direct epimerization reaction were not observed in each reaction. These results strongly indicated that the endo adducts are kinetically favored products in the present DA reaction.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.