Rhodium catalysed tandem conjugate addition-protonation: An enantioselective synthesis of 2-substituted succinic esters

Chemical Communications

Volumn , Issue 17, 2004, Pages 1984-1985

  Moss, Rebecca J ^a   Wadsworth, Kelly J ^a   Chapman, Christopher J ^a   Frost, Christopher G ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BORIC ACID; DIMETHYL ITACONATE; ESTER; ITACONIC ACID; POTASSIUM TRIFLUOROORGANOBORATE; RHODIUM; SUCCINIC ACID; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOMER; ENANTIOSELECTIVITY; PROTON TRANSPORT; SYNTHESIS;

EID: 5044232333     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b406905f     Document Type: Article

References (18)

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5. Hayashi has reported that 1-nitrocyclohexene is a satisfactory substrate in the enantioselective addition affording products with high enantioselectivity and good diastereoselectivity controlled by protonation: T. Hayashi, T. Senda and M. Ogasawara, J. Am. Chem. Soc., 2000, 122, 10716.
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12. See electronic supporting information for details.
13. For a review see: S. Darses and J.-P. Genêt, Eur. J. Org. Chem., 2003, 4313.
14. 1Pr-PHOSOX (10%), ChiraPHOS(<5%).
15. The two diastereomeric oxa-π-allyl intermediates could interconvert by a π-σ-π mechanism: S. H. Bergens and B. Bosnich, J. Am. Chem. Soc., 1991, 113, 958.
16. M. Pucheault, S. Darses and J.-P. Genêt, Eur. J. Org. Chem., 2002, 3552.
17. A range of 2,6-disubstituted phenols were also tested resulting in modest enantioselectivities (20-45%).
18. High yields of racemic product 3a are obtained at 60 °C and 80 °C with either pre-formed complexes or those prepared in situ.