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Volumn 49, Issue 46, 2010, Pages 8712-8716

Regioselective nickel-catalyzed reductive couplings of enones and allenes

Author keywords

allenes; conjugate addition; nickel; reductive coupling; regioselectivity

Indexed keywords

ALLENES; CONJUGATE ADDITION; COUPLING PROCESS; REDUCTIVE COUPLINGS; REGIO-SELECTIVE; SOLVENT COMPOSITION; TERMINAL ALKYNE;

EID: 78149460897     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201004740     Document Type: Article
Times cited : (25)

References (67)
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    • For related processes, see
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    • note
    • A single example of the catalytic addition of 1-octene to a β-unsubstituted enone was previously reported by Jamison and co-workers (reference[5]). The reaction afforded enol silanes with the 1,1- and 1,2-disubstitution pattern as a 4:1 mixture of regioisomers 4 and 2. Aromatic alkynes cleanly provided the 1,2-disubstituted isomer 2. As this procedure was largely developed for ethylene additions to generate product 3, the generality with alkyl-substituted olefins for obtaining the 1,1-disubstitution pattern (4) across a range of substrates was not established in this report. The report from Ogoshi et al. (reference[6]) illustrated that, without silyl triflate promoters and using β-substituted enones, the 1,2-disubstituted isomer 2 was exclusively obtained, irrespective of the electronic nature of the alkene.
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    • note
    • Jamison has extensively developed the synthesis of 1,1-disubstituted alkenes by catalytic alkene additions to aldehydes
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    • For other entries to substructure 4 with a 1,1-disubstituted alkene
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.