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Volumn 43, Issue 9, 2004, Pages 1048-1052

Asymmtetric cycloisomerization of 1,6- and 1,7-enynes by transition-metal catalysts

Author keywords

Atom economy; Cyclization; Enantioselectivity; Palladium; Rhodium; Ruthenium

Indexed keywords

CATALYSIS; ENVIRONMENTAL PROTECTION; SYNTHESIS (CHEMICAL); TRANSITION METALS;

EID: 4344685383     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200301699     Document Type: Review
Times cited : (155)

References (29)
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    • The thermal Alder reaction, in the absence of a transition metal, has had few applications in organic synthesis, due to limitations in scope, particularly as extremely high temperatures are required.
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    • A. Goeke, M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1996, 108, 686; Angew. Chem. Int. Ed. Engl. 1996, 35, 662 [trap = 2,2″-bis[1- (diarylphosphanyl)-ethyl]-1,1″-biferrocene].
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    • A. Goeke, M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1996, 108, 686; Angew. Chem. Int. Ed. Engl. 1996, 35, 662 [trap = 2,2″-bis[1- (diarylphosphanyl)-ethyl]-1,1″-biferrocene].
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    • M. Hatano, M. Terada, K. Mikami, Angew. Chem. 2001, 113, 255; Angew. Chem. Int. Ed. 2001, 40, 249 [binap = 2,2′-bis(diphenylphosphanyl)-1, 1′-binaphthyl), chiraphos = 2,3-bis(diphenylphosphanyl)butane, diop = 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphanyl)butane].
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    • M. Hatano, M. Terada, K. Mikami, Angew. Chem. 2001, 113, 255; Angew. Chem. Int. Ed. 2001, 40, 249 [binap = 2,2′-bis(diphenylphosphanyl)-1, 1′-binaphthyl), chiraphos = 2,3-bis(diphenylphosphanyl)butane, diop = 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphanyl)butane].
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    • P. Cao, X. Zhang, Angew. Chem. 2000, 112, 4270; Angew. Chem. Int. Ed. 2000, 39, 4104 [duphos = 1,2-bis(phospholano)benzene, bicp = 2,2′-bis(diphenylphosphanyl)-1,1′-dicyclopentane, bicpo = 2,2′-bis(diphenylphosphinite)-1,1′-dicyclopentane].
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    • P. Cao, X. Zhang, Angew. Chem. 2000, 112, 4270; Angew. Chem. Int. Ed. 2000, 39, 4104 [duphos = 1,2-bis(phospholano)benzene, bicp = 2,2′-bis(diphenylphosphanyl)-1,1′-dicyclopentane, bicpo = 2,2′-bis(diphenylphosphinite)-1,1′-dicyclopentane].
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    • Pd-catalyzed asymmetric cyclization of similar enynes initiated by acetoxypalladation results in β-deacetoxypalladation (elimination). This protocol is very useful for the asymmetric synthesis of substituted γ-butyrolactones, see: a) Q. Zhang, X. Lu, X. Han, J. Org. Chem. 2001, 66, 7676;
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    • H. Chakrapani, C. Liu, R. A. Widenhoefer, Org. Lett. 2003, 5, 157. It was found that Rh/binap complexes were not effective catalysts for cyclization/ hydrosilation. [biphemp = 6,6′-bis-(diphenylphosphanyl)-2,2′- dimethyl-biphenyll.
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    • note
    • The presence of phosphane ligands with this catalyst might slow down the rate of cycloisomerization.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.