Open AccessAn efficient, palladium-catalyzed, enantioselective synthesis of (2 R )-3-butene-1,2-diol and its use in highly selective Heck reactions
Author(s) -
Natasha Cheeseman,
Martin E. Fox,
Mark Jackson,
Ian C. Len,
Graham Meek
Publication year - 2004
Publication title -
proceedings of the national academy of sciences of the united states of america
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.0307047101
Subject(s) - palladium , catalysis , diol , 2 butene , yield (engineering) , chemistry , enantioselective synthesis , heck reaction , 1 butene , enantiomer , coupling reaction , organic chemistry , combinatorial chemistry , materials science , metallurgy
A robust and scalable procedure for the palladium-catalyzed dynamic kinetic asymmetric transformation of 3,4-epoxy-1-butene into (2R)-3-butene-1,2-diol with water as the cosolvent is reported. Examination of the effects of solvent and temperature led to the identification of conditions that permitted use of 0.025 mol % catalyst, providing (2R)-3-butene-1,2-diol in 84% isolated yield and 85% enantiomeric excess. Subsequent Heck reactions with a diverse range of coupling partners are described and the influence of their electronic nature on maintaining the enantiopurity of the diol is discussed.