Stereodivergent catalytic doubly diastereoselective nitroaldol reactions using heterobimetallic complexes |
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Authors: | Sohtome Yoshihiro Kato Yuko Handa Shinya Aoyama Naohiro Nagawa Keita Matsunaga Shigeki Shibasaki Masakatsu |
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Institution: | Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Tokyo, Japan. |
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Abstract: | Stereodivergent construction of three contiguous stereocenters in catalytic doubly diastereoselective nitroaldol reactions of alpha-chiral aldehydes with nitroacetaldehyde dimethyl acetal using two types of heterobimetallic catalysts is described. A La-Li-BINOL (LLB) catalyst afforded anti,syn-nitroaldol products in >20:1-14:1 selectivity, and a Pd/La/Schiff base catalyst afforded complimentary syn,syn-nitroaldol products in 10:1-5:1 selectivity. |
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