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Enantioselective rhodium-catalyzed conjugate alkynylation of 5-benzylidene Meldrum's acids with TMS-acetylene.
J Am Chem Soc. 2009 Oct 21; 131(41):14608-9.JA

Abstract

The enantioselective alkynylation of benzylidene Meldrum's acids has been successfully achieved through rhodium-catalyzed addition of TMS-acetylene in the presence of bisphosphine ligand 3,5-Xylyl-MeOBIPHEP. The resulting Meldrum's acids were obtained in good yields and up to 99% enantiomeric excess. The alkynylation method is carried out under mild reactions conditions and is compatible with an array of functional groups.

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Authors+Show Affiliations

Fillion E
Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1. efillion@uwaterloo.ca
Zorzitto AK
No affiliation info available

MeSH

AcetyleneAlkynesCatalysisDioxanesRhodiumStereoisomerismSubstrate Specificity

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19824719

Citation

Fillion, Eric, and Alexander K. Zorzitto. "Enantioselective Rhodium-catalyzed Conjugate Alkynylation of 5-benzylidene Meldrum's Acids With TMS-acetylene." Journal of the American Chemical Society, vol. 131, no. 41, 2009, pp. 14608-9.
Fillion E, Zorzitto AK. Enantioselective rhodium-catalyzed conjugate alkynylation of 5-benzylidene Meldrum's acids with TMS-acetylene. J Am Chem Soc. 2009;131(41):14608-9.
Fillion, E., & Zorzitto, A. K. (2009). Enantioselective rhodium-catalyzed conjugate alkynylation of 5-benzylidene Meldrum's acids with TMS-acetylene. Journal of the American Chemical Society, 131(41), 14608-9. https://doi.org/10.1021/ja905336p
Fillion E, Zorzitto AK. Enantioselective Rhodium-catalyzed Conjugate Alkynylation of 5-benzylidene Meldrum's Acids With TMS-acetylene. J Am Chem Soc. 2009 Oct 21;131(41):14608-9. PubMed PMID: 19824719.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective rhodium-catalyzed conjugate alkynylation of 5-benzylidene Meldrum's acids with TMS-acetylene. AU - Fillion,Eric, AU - Zorzitto,Alexander K, PY - 2009/10/15/entrez PY - 2009/10/15/pubmed PY - 2010/1/12/medline SP - 14608 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 131 IS - 41 N2 - The enantioselective alkynylation of benzylidene Meldrum's acids has been successfully achieved through rhodium-catalyzed addition of TMS-acetylene in the presence of bisphosphine ligand 3,5-Xylyl-MeOBIPHEP. The resulting Meldrum's acids were obtained in good yields and up to 99% enantiomeric excess. The alkynylation method is carried out under mild reactions conditions and is compatible with an array of functional groups. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/19824719/Enantioselective_rhodium_catalyzed_conjugate_alkynylation_of_5_benzylidene_Meldrum's_acids_with_TMS_acetylene_ L2 - https://doi.org/10.1021/ja905336p DB - PRIME DP - Unbound Medicine ER -