TY - JOUR
T1 - Direct catalytic asymmetric aldol reactions of thioamides
T2 - Toward a stereocontrolled synthesis of 1,3-polyols
AU - Iwata, Mitsutaka
AU - Yazaki, Ryo
AU - Suzuki, Yuta
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
PY - 2009/12/30
Y1 - 2009/12/30
N2 - (Chemical Equation Presented) A direct catalytic asymmetric aldol reaction of thioamides with a soft Lewis acid/hard Brønsted base cooperative catalytic system comprising (R,R)-Ph-BPE/[Cu(CH3CN) 4]PF6/LiOAr is described. Highly chemoselective deprotonative activation of thioamides allows for a direct aldol reaction of α-nonbranched aliphatic aldehydes, which are susceptible to self-condensation. Facile reduction of the thioamide functionality and a catalyst-controlled second aldol reaction provides 1,3-diols in a highly stereoselective manner.
AB - (Chemical Equation Presented) A direct catalytic asymmetric aldol reaction of thioamides with a soft Lewis acid/hard Brønsted base cooperative catalytic system comprising (R,R)-Ph-BPE/[Cu(CH3CN) 4]PF6/LiOAr is described. Highly chemoselective deprotonative activation of thioamides allows for a direct aldol reaction of α-nonbranched aliphatic aldehydes, which are susceptible to self-condensation. Facile reduction of the thioamide functionality and a catalyst-controlled second aldol reaction provides 1,3-diols in a highly stereoselective manner.
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U2 - 10.1021/ja909758e
DO - 10.1021/ja909758e
M3 - Article
C2 - 19994862
AN - SCOPUS:73249116580
VL - 131
SP - 18244
EP - 18245
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 51
ER -