Synthesis of beta,beta-disubstituted vinyl boronates via the ruthenium-catalyzed Alder ene reaction of borylated alkynes and alkenes.
J Am Chem Soc. 2005 Mar 16; 127(10):3252-3.JA

Abstract

Ruthenium-catalyzed Alder ene reactions between borylated alkynes and terminal alkenes give the corresponding beta,beta-disubstituted vinyl boronates with high selectivity for the branched isomer. The stereochemistry of the vinyl boronate moiety was the result of a formal trans addition of the ene subunit across the alkyne, which is the opposite stereochemical outcome observed for other internal alkynes.

Authors+Show Affiliations

Hansen EC

Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.

Lee D

No affiliation info available

MeSH

AlkenesAlkynesBoronic AcidsCatalysisRutheniumVinyl Compounds

Pub Type(s)

Journal Article

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

Research Support, U.S. Gov't, Non-P.H.S.

Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15755122

Citation

Hansen, Eric C., and Daesung Lee. "Synthesis of Beta,beta-disubstituted Vinyl Boronates Via the Ruthenium-catalyzed Alder Ene Reaction of Borylated Alkynes and Alkenes." Journal of the American Chemical Society, vol. 127, no. 10, 2005, pp. 3252-3.

Hansen EC, Lee D. Synthesis of beta,beta-disubstituted vinyl boronates via the ruthenium-catalyzed Alder ene reaction of borylated alkynes and alkenes. J Am Chem Soc. 2005;127(10):3252-3.

Hansen, E. C., & Lee, D. (2005). Synthesis of beta,beta-disubstituted vinyl boronates via the ruthenium-catalyzed Alder ene reaction of borylated alkynes and alkenes. Journal of the American Chemical Society, 127(10), 3252-3.

Hansen EC, Lee D. Synthesis of Beta,beta-disubstituted Vinyl Boronates Via the Ruthenium-catalyzed Alder Ene Reaction of Borylated Alkynes and Alkenes. J Am Chem Soc. 2005 Mar 16;127(10):3252-3. PubMed PMID: 15755122.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Synthesis of beta,beta-disubstituted vinyl boronates via the ruthenium-catalyzed Alder ene reaction of borylated alkynes and alkenes. AU - Hansen,Eric C, AU - Lee,Daesung, PY - 2005/3/10/pubmed PY - 2005/6/4/medline PY - 2005/3/10/entrez SP - 3252 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 127 IS - 10 N2 - Ruthenium-catalyzed Alder ene reactions between borylated alkynes and terminal alkenes give the corresponding beta,beta-disubstituted vinyl boronates with high selectivity for the branched isomer. The stereochemistry of the vinyl boronate moiety was the result of a formal trans addition of the ene subunit across the alkyne, which is the opposite stereochemical outcome observed for other internal alkynes. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/15755122/Synthesis_of_betabeta_disubstituted_vinyl_boronates_via_the_ruthenium_catalyzed_Alder_ene_reaction_of_borylated_alkynes_and_alkenes_ DB - PRIME DP - Unbound Medicine ER -

Tags

Synthesis of beta,beta-disubstituted vinyl boronates via the ruthenium-catalyzed Alder ene reaction of borylated alkynes and alkenes.J Am Chem Soc. 2005 Mar 16; 127(10):3252-3.JA