TY - JOUR
T1 - A direct catalytic asymmetric aldol reaction of α-sulfanyl lactones
T2 - Efficient synthesis of SPT inhibitors
AU - Takechi, Sho
AU - Yasuda, Shigeo
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
PY - 2012/4/23
Y1 - 2012/4/23
N2 - Softly does it: The title reaction, catalyzed by a AgPF 6/(R)- biphep-type ligand/DBU complex, is described (see scheme). This protocol gives efficient access to syn-configured α-sulfanyl-β-hydroxy lactones in a highly enantioselective manner. In one particular case, the sulfide group was stereospecifically replaced with a hydroxy group to afford an enantioenriched tertiary alcohol, which upon further manipulation led to a class of densely functionalized SPT inhibitors.
AB - Softly does it: The title reaction, catalyzed by a AgPF 6/(R)- biphep-type ligand/DBU complex, is described (see scheme). This protocol gives efficient access to syn-configured α-sulfanyl-β-hydroxy lactones in a highly enantioselective manner. In one particular case, the sulfide group was stereospecifically replaced with a hydroxy group to afford an enantioenriched tertiary alcohol, which upon further manipulation led to a class of densely functionalized SPT inhibitors.
KW - SPT inhibitor
KW - aldol reaction
KW - asymmetric catalysis
KW - silver
KW - sulfanyl lactone
UR - http://www.scopus.com/inward/record.url?scp=84859970264&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84859970264&partnerID=8YFLogxK
U2 - 10.1002/anie.201200520
DO - 10.1002/anie.201200520
M3 - Article
C2 - 22415971
AN - SCOPUS:84859970264
SN - 1433-7851
VL - 51
SP - 4218
EP - 4222
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 17
ER -