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Formation of multi-stereogenic centers using a catalytic diastereoselective Henry reaction
Takayoshi Arai1, Yoshinori Taneda, Yoko Endo
1Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan. tarai@faculty.chiba-u.jp
Abstract:
A diastereoselective Henry reaction of chiral aldehydes with nitroalkanes was developed using a chiral sulfonyldiamine (L1)-CuCl complex. The reaction of (R)-2-phenylpropanal and nitromethane was smoothly catalyzed by the (S,S,S)-L1-CuCl complex to give the adduct with 99/1 syn/anti selectivity in 99% ee. In the reaction of (S)-2-phenylpropanal and nitroethane, the (R,R,R)-L1-CuCl catalyst yielded the expected three contiguous stereogenic centers in a highly syn-selective Henry reaction.
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