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Volumn 13, Issue 5, 2007, Pages 1350-1357

Recent developments in the metal-catalyzed reactions of metallocarbenoids from propargylic esters

Author keywords

Carbenoids; Enynes; Natural products; Rautenstrauch cyclopropanation; Transition metals

Indexed keywords

COMPUTATION THEORY; ESTERS; ISOMERIZATION; KETONES; MOLECULAR STRUCTURE;

EID: 34047228439     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601522     Document Type: Article
Times cited : (249)

References (63)
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    • We propose this term (Rautenstrauch cyclopropanation) in order to clearly differentiate it from the palladium-catalyzed cyclization of 1-ethynyl-2-propenyl acetates to give 1,4-cyclopentadienyl acetates, which afford 2-cyclopentanones, a process that we propose to name as Rautenstrauch pentannulation: a) see reference [4a];
    • We propose this term ("Rautenstrauch cyclopropanation") in order to clearly differentiate it from the palladium-catalyzed cyclization of 1-ethynyl-2-propenyl acetates to give 1,4-cyclopentadienyl acetates, which afford 2-cyclopentanones, a process that we propose to name as "Rautenstrauch pentannulation": a) see reference [4a];
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    • For related 1, 3-diynes, see
    • For related 1, 3-diynes, see: E. J. Cho, M. Kim, D. Lee, Org. Lett. 2006, 8, 5413-5416.
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    • Angew. Chem. Int. Ed. 2006, 45, 2901-2904. In this preliminary communication, Fehr and Galindo have also synthesized enantiomerically pure precursors I and II and then submitted them to cyclization giving rise to some unexpected results; this prompted them to suggest that Soriano/Marco-Contelles' proposal for the mechanism of the Rautenstrauch cyclopropanation (reference [18]) should be re-considered; their mechanistic proposal has been recently re-analyzed by us (reference [22]).
    • Angew. Chem. Int. Ed. 2006, 45, 2901-2904. In this preliminary communication, Fehr and Galindo have also synthesized enantiomerically pure precursors I and II and then submitted them to cyclization giving rise to some unexpected results; this prompted them to suggest that Soriano/Marco-Contelles' proposal for the mechanism of the Rautenstrauch cyclopropanation (reference [18]) should be re-considered; their mechanistic proposal has been recently re-analyzed by us (reference [22]).
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    • The conclusions from a recent DFT study on chiral precursors 31 and 33, and others, support the mechanism shown in Scheme 9B as the favored path, and suggest that the degree of chirality transfer depends on the nature and stereochemistry of the starting enyne. On Accounting for the Stereoselective Control of the Metal-Catalyzed Rautenstrauch Cyclopropanation E. Soriano, J. Marco-Contelles, unpublished results.
    • The conclusions from a recent DFT study on chiral precursors 31 and 33, and others, support the mechanism shown in Scheme 9B as the favored path, and suggest that the degree of chirality transfer depends on the nature and stereochemistry of the starting enyne. ("On Accounting for the Stereoselective Control of the Metal-Catalyzed Rautenstrauch Cyclopropanation" E. Soriano, J. Marco-Contelles, unpublished results.
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    • a) B. A. B. Prasad, F. K. Yoshimoto, R. Sarpong, J. Am. Chem. Soc. 2005, 127, 12 468-12 469. This chemistry has been extended with success to open-chain molecules and non-aromatic ring systems:
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    • in a recent communication Zhang has described the gold-catalyzed formation of alkenyl enol esters from trimethylsilylmethyl-substituted propargylic esters: S. Wang, L. Zhang, Org. Lett. 2006, 8, 4585-4587
    • b) in a recent communication Zhang has described the gold-catalyzed formation of alkenyl enol esters from trimethylsilylmethyl-substituted propargylic esters: S. Wang, L. Zhang, Org. Lett. 2006, 8, 4585-4587.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.