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Volumn 49, Issue 27, 2010, Pages 4633-4637

Gold(I)-catalyzed enantioselective synthesis of functionalized indenes

Author keywords

Asymmetric catalysis; C C coupling; Cyclization; Gold; Indenes

Indexed keywords

ALKOXYCYCLIZATION; ALKYNYLS; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; C-C COUPLING; CHEMICAL EQUATIONS; CYCLOISOMERIZATIONS; ENANTIOSELECTIVE SYNTHESIS; FUNCTIONALIZED; MILD REACTION CONDITIONS; STYRENE DERIVATIVES;

EID: 77953936776     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201001089     Document Type: Article
Times cited : (134)

References (54)
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    • Liu and co-workers have reported the ruthenium-catalyzed cycloisomerization of 2′, 2′ -disubstituted o-(ethynyl)styrenes to afford, 2-alkenyl-1H-indenes as major adducts. The reaction is proposed to occur through a cascade process initiated by 5-endo cyclization of the initially formed ruthenium-vinylidene species and subsequent "methylenecyclopropane- trimethylenemethane" rearrangement: R. J. Madhushaw, C.-Y. Lo, C.-W. Hwang, M.-D. Su, H.-C. Shen, S. Pal, I. R. Shaikh, R.-S. Liu, J. Am. Chem. Soc. 2004, 126, 15560-15565. These results are in sharp contrast with the total selectivity to give naphthalene derivatives through a 6-endo cyclization reaction observed with the same ruthenium catalyst when non disubstituted o-(alkynyl)styrenes are used as starting materials (see reference [13]).
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    • The scope of this new transformation was briefly investigated using different o-alkynyl styrenes 1a-h. See the Supporting Information for the synthesis of racemic 1-alkenyl-1H-indenes 2a-g and 1-oxygen-functionalized-1H- indenes 3aa-3hb In addition, we also looked at the behavior of the corresponding terminal alkyne, 2′,2′-dimethyl o-(ethynyl)styrene, though the reaction was sluggish and gave decomposition products
    • The scope of this new transformation was briefly investigated using different o-alkynyl styrenes 1a-h. See the Supporting Information for the synthesis of racemic 1-alkenyl-1H-indenes 2a-g and 1-oxygen-functionalized-1H- indenes 3aa-3hb. In addition, we also looked at the behavior of the corresponding terminal alkyne, 2′,2′-dimethyl o-(ethynyl)styrene, though the reaction was sluggish and gave decomposition products.
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    • ortho-(Alkynyl)styrenes could be considered in some way as 1,5enynes. As far as we know neither the gold-catalyzed enantioselective cycloisomerization of o-(alkynyl)styrenes neither of 1,5-enynes has been reported. In contrast, gold-catalyzed enantioselective reactions of 1,6-enynes have been described (see references [21a,c,d])
    • ortho-(Alkynyl)styrenes could be considered in some way as 1,5enynes. As far as we know neither the gold-catalyzed enantioselective cycloisomerization of o-(alkynyl)styrenes neither of 1,5-enynes has been reported. In contrast, gold-catalyzed enantioselective reactions of 1,6-enynes have been described (see references [21a,c,d]).
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    • CCDC 766525 (3ha) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
    • Cambridge Crystallographic Data Centre


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.