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Volumn 10, Issue 8, 2008, Pages 1521-1523

Highly regioselective synthesis of trisubstituted allenes via lithiation of 1-Aryl-3-alkylpropadiene, subsequent transmetalation, and Pd-catalyzed negishi coupling reaction

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EID: 54549121958     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8001909     Document Type: Article
Times cited : (14)

References (28)
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    • Ma, S. Eur. J. Org. Chem. 2004, 1175 and references cited therein. For some early references involving the cross coupling of propargyl/l,2-allenylpalladium species with organozinc species, see: Ruitenburg, T.; Kleijn, H; Elservier, C. J.; Vermeer, P. Tetrahedron Lett. 1981, 22, 1451. Elservier, C. J.; Mooiweer, H. H.; Kleijn, H.; Vermeer, P. Tetrahedron Lett. 1984, 25, 5571.
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    • Zinc: see ref 3g,h
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  • 24
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    • For pioneering studies on the lithiation of simple allenes, see: a
    • For pioneering studies on the lithiation of simple allenes, see: (a) Michelot, D.; Linstrumelle, G. J. Chem. Soc., Chem. Commun. 1975, 561.
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    • The assignment of the regioselectivity was based on the distinct coupling constant of the two different allenic hydrogens
    • The assignment of the regioselectivity was based on the distinct coupling constant of the two different allenic hydrogens.


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