Prostereogenic face and orientation selective oxidative coupling reaction between methyl methacrylate and 2,5-dihydrofuran catalyzed by a ruthenium(0) compound

Organometallics

Volumn 30, Issue 6, 2011, Pages 1307-1310

  Hiroi, Yuki ^a   Komine, Nobuyuki ^a   Hirano, Masafumi ^a   Komiya, Sanshiro ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVE; DIHYDROFURANS; METHYL METHACRYLATES; OXIDATIVE COUPLING REACTIONS; TRANSITION-METAL CENTERS;

CATALYSIS; COORDINATION REACTIONS; ESTERS; NAPHTHALENE; OLEFINS; RUTHENIUM; TRANSITION METALS;

ACRYLIC MONOMERS;

EID: 79952954441     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200091n     Document Type: Article

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39. A reviewer suggested coordination of the oxygen in 2,3-dihydrofuran would also be a reasonable reason for the present diastereoselectivity. However, we believe this possibility to be less likely because the highly Lewis basic Ru(0) species generally favors π-acidic substrates such as olefins.
40. Alternatively, these fragments may be placed in the same direction to avoid steric repulsion between them and the 1,5-COD ligand. However, we believe this is the less likely orientation, because this orientation causes steric repulsion at the C-C bond-forming step and such electrocyclic reactions are generally very sensitive to steric repulsion.