TY - JOUR
T1 - Solvent-Dependent Enantiodivergence in anti-Selective Catalytic Asymmetric Nitroaldol Reactions
AU - Karasawa, Tomoya
AU - Saito, Akira
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
N1 - Funding Information:
This work was financially supported by KAKENHI (17H03025 and 18H04276 in Precisely Designed Catalysts with Customized Scaffolding) from JSPS and MEXT. We are grateful to Dr. Ryuichi Sawa, Ms. Yumiko Kubota, and Dr. Kiyoko Iijima at the Institute of Microbial Chemistry for NMR analysis.
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/5/17
Y1 - 2019/5/17
N2 - anti-Selective catalytic asymmetric nitroaldol reactions of α-keto esters promoted by a heterogeneous Nd/Na heterobimetallic catalyst exhibited a significant, unexpected disparity in enantioselection that was solvent-dependent. This phenomenon exclusively occurred when the stereogenic center of a diamide ligand had the smallest substituent (Me group, derived from l-Ala), which behaved uniquely in comparison with other structurally similar ligands to provide antipodal products under otherwise identical conditions.
AB - anti-Selective catalytic asymmetric nitroaldol reactions of α-keto esters promoted by a heterogeneous Nd/Na heterobimetallic catalyst exhibited a significant, unexpected disparity in enantioselection that was solvent-dependent. This phenomenon exclusively occurred when the stereogenic center of a diamide ligand had the smallest substituent (Me group, derived from l-Ala), which behaved uniquely in comparison with other structurally similar ligands to provide antipodal products under otherwise identical conditions.
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U2 - 10.1021/acs.orglett.9b00982
DO - 10.1021/acs.orglett.9b00982
M3 - Article
C2 - 30995054
AN - SCOPUS:85065043186
VL - 21
SP - 3581
EP - 3583
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 10
ER -