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One‐Pot Three‐Component Catalytic Enantioselective Synthesis of Homoallylboronates
Author(s) -
Ibrahem Ismail,
Breistein Palle,
Córdova Armando
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201105458
Subject(s) - enantioselective synthesis , component (thermodynamics) , catalysis , chemistry , combinatorial chemistry , organic chemistry , physics , thermodynamics
No longer a simple bor(ation) : The title reaction between bis(pinacolato)diboron, enals, and 2‐(triphenylphosphoranylidene)acetates employing bench‐stable copper salts and a simple chiral amine co‐catalyst is presented (see scheme). The reaction proceeds through a catalytic asymmetric conjugate borane addition/Wittig sequence wherein the β‐boration step is 1,4‐selective and gives the corresponding homoallylboronate products with high enantiomeric ratios.