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Volumn 50, Issue 19, 2011, Pages 4475-4479

Rhodium-catalyzed asymmetric formal olefination or cycloaddition: 1,3-dicarbonyl compounds reacting with 1,6-diynes or 1,6-enynes

Author keywords

asymmetric catalysis; cycloaddition; enynes; olefination; rhodium

Indexed keywords

[2+2+2] CYCLOADDITION; ASYMMETRIC CATALYSIS; BINAPHTHYL; DICARBONYL COMPOUNDS; ELECTROCYCLIC RINGS; ENYNES; OLEFINATION; RHODIUM COMPLEXES; RHODIUM-CATALYZED;

EID: 79955487595     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201007727     Document Type: Article
Times cited : (27)

References (64)
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    • Recently, the organocatalyzed asymmetric aldolization of 2-oxo-3-aryl-succinates through C-C/O-H bond formation of the ketone carbonyl group was reported. See:, Y. Wang, Z. Shen, B. Li, Y. Zhang, Y. Zhang, Chem. Commun. 2007, 1284.
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    • We have recently reported the rhodium-catalyzed [2+2+2] cycloaddition of a 1,6-diyne with acetylacetone and methyl acetoacetate. See: Ref. [8c].
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    • The product olefin geometry is determined primarily through thermodynamic control of the electrocyclic ring-opening reaction. However, the other relies on the influence of the cationic rhodium(I) complex or silica gel during the reaction or the product isolation, respectively. For thermodynamic control of stereoselectivity in the electrocyclic ring opening of (2H)-pyran, see
    • The product olefin geometry is determined primarily through thermodynamic control of the electrocyclic ring-opening reaction. However, the other relies on the influence of the cationic rhodium(I) complex or silica gel during the reaction or the product isolation, respectively. For thermodynamic control of stereoselectivity in the electrocyclic ring opening of (2H)-pyran, see
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    • See the Supporting information for details.
    • See the Supporting information for details.
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    • CCDC 803849 [(3aR,5aR,6R)-(-)- 8 ] and 811124 [(±)- 9 ] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • CCDC 803849 [(3aR,5aR,6R)-(-)- 8 ] and 811124 [(±)- 9 ] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
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    • Although the reaction of a tosylamide-linked terminal 1,6-diyne and 2 a was also examined, the corresponding formal olefination product was not obtained at all because of the rapid homo-[2+2+2] cycloaddition of the diyne.
    • Although the reaction of a tosylamide-linked terminal 1,6-diyne and 2 a was also examined, the corresponding formal olefination product was not obtained at all because of the rapid homo-[2+2+2] cycloaddition of the diyne.
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    • Fused 5-6-6 oxaheterocycles, which are closely related to compounds 7, are found in several biologically active natural products. See
    • Fused 5-6-6 oxaheterocycles, which are closely related to compounds 7, are found in several biologically active natural products. See


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.