Half-sandwich rhodium (and iridium) complexes as enantioselective catalysts for the 1,3-dipolar cycloaddition of 3,4-dihydroisoquinoline N-oxide to methacrylonitrile.

Half-sandwich rhodium (and iridium) complexes as enantioselective catalysts for the 1,3-dipolar cycloaddition of 3,4-dihydroisoquinoline N-oxide to methacrylonitrile. Research Abstract Details 

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Half-sandwich rhodium (and iridium) complexes as enantioselective catalysts for the 1,3-dipolar cycloaddition of 3,4-dihydroisoquinoline N-oxide to methacrylonitrile. Abstract Text:

Daniel Carmona,M Pilar Lamata,Fernando Viguri,Ricardo ,Fernando J Lahoz,Luis A Oro,Daniel Carmona,M Pilar Lamata,Fernando Viguri,Ricardo Rodríguez,Fernando J Lahoz,Luis A Oro,

Cationic half-sandwich complexes containing the [(eta(5)-C(5)Me(5))M(Diphos*)] moiety (M=Rh, Ir; Diphos*=chiral diphosphine ligand) catalyze the cycloaddition of the nitrone 3,4-dihydroisoquinoline N-oxide (A) to methacrylonitrile (B) with excellent regio and endo selectivity and low-to-moderate enantioselectivity. The most active and selective catalyst, (S(Rh),R(C))-[(eta(5)-C(5)Me(5))Rh{(R)-Prophos)} (NC(Me)C==CH(2))](SbF(6))(2), has been isolated and fully characterized including the determination of the molecular structure by X-ray diffraction. The R-at-metal epimers of the complexes [(eta(5)-C(5)Me(5))M{(R)-Prophos)}(NC(Me)C==CH(2))](SbF(6))(2) (M=Rh, Ir) isomerize to the corresponding S-at-metal diastereomers. The stoichiometric cycloaddition of A with B is catalyzed by diastereopure (S(M),R(C))-[(eta(5)-C(5)Me(5))M{(R)-Prophos)}(NC(Me)C==CH(2))](SbF(6))(2) with perfect regio and endo selectivity and very good (up to 95 %) ee. The catalyst can be recycled up to nine times without significant loss of either activity or selectivity.

Half-sandwich rhodium (and iridium) complexes as enantioselective catalysts for the 1,3-dipolar cycloaddition of 3,4-dihydroisoquinoline N-oxide to methacrylonitrile. Publishing Authors By Initials

D Carmona,MP Lamata,F Viguri,R ,FJ Lahoz,LA Oro,D Carmona,MP Lamata,F Viguri,R Rodríguez,FJ Lahoz,LA Oro,

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Half-sandwich rhodium (and iridium) complexes as enantioselective catalysts for the 1,3-dipolar cycloaddition of 3,4-dihydroisoquinoline N-oxide to methacrylonitrile. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)

VOLUME: 13

Page Numbers: 9746-56

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ISSN: 0947-6539

DAY: 6

MONTH: 12

YEAR: 2007

Half-sandwich rhodium (and iridium) complexes as enantioselective catalysts for the 1,3-dipolar cycloaddition of 3,4-dihydroisoquinoline N-oxide to methacrylonitrile. Information

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LANGUAGE: eng

NlmUniqueID: 9513783

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Grant and Affiliation Information for Half-sandwich rhodium (and iridium) complexes as enantioselective catalysts for the 1,3-dipolar cycloaddition of 3,4-dihydroisoquinoline N-oxide to methacrylonitrile.

AFFILIATION: Departamento de Química Inorgánica, Instituto Universitario de Catálisis Homogénea, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza-Consejo Superior de Investigaciones Científicas, Zaragoza, Spain. dcarmona@unizar.es

Country: Germany

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MEDLINETA: Chemistry

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