TY - JOUR
T1 - Copper-catalysed domino silylative aldol reaction leading to stereocontrolled chiral quaternary carbons
AU - Welle, Alexandre
AU - Petrignet, Julien
AU - Tinant, Bernard
AU - Wouters, Johan
AU - Riant, Olivier
PY - 2010/9/24
Y1 - 2010/9/24
N2 - (Chemical Equation Presented) Asymmetric aldol reaction: A domino silylation-aldol reaction between enoyloxazolidinones and various aldehydes has been developed (see scheme). The process catalysed by a copper complex in the presence of a borosilane led to high diastereoselectivities. Yields between 59 and 90 % and d.r. values between 78:22 to 95:5 were obtained. When methacryloyloxazolidinones were used, a controlled chiral quaternary carbon was generated. BPin=4,4,5,5-tetramethyl-1,3,2dioxaborolan-2-yl.
AB - (Chemical Equation Presented) Asymmetric aldol reaction: A domino silylation-aldol reaction between enoyloxazolidinones and various aldehydes has been developed (see scheme). The process catalysed by a copper complex in the presence of a borosilane led to high diastereoselectivities. Yields between 59 and 90 % and d.r. values between 78:22 to 95:5 were obtained. When methacryloyloxazolidinones were used, a controlled chiral quaternary carbon was generated. BPin=4,4,5,5-tetramethyl-1,3,2dioxaborolan-2-yl.
KW - Aldol reaction
KW - Asymmetric synthesis
KW - Copper
KW - Quaternary stereocenters
KW - Silylation
UR - http://www.scopus.com/inward/record.url?scp=77956960443&partnerID=8YFLogxK
U2 - 10.1002/chem.201000907
DO - 10.1002/chem.201000907
M3 - Article
AN - SCOPUS:77956960443
SN - 0947-6539
VL - 16
SP - 10980
EP - 10983
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
IS - 36
ER -