| Budget Amount *help |
¥18,590,000 (Direct Cost: ¥14,300,000、Indirect Cost: ¥4,290,000)
Fiscal Year 2013: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2012: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2011: ¥7,670,000 (Direct Cost: ¥5,900,000、Indirect Cost: ¥1,770,000)
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| Research Abstract |
In this study, we have succeeded a novel one-pot process for alpha-amino acid synthesis from imine precursors using Me3SiSnBu3 or PhMe2SiBpin in the presence of CsF. Also, a catalytic enantioselective silylation of N-t-butylsulfonylimines using a copper-diamine complex was realized, and the resulting optically active alpha-amino silanes could be carboxylated under a CO2 atmosphere (1 atm) to afford the corresponding alpha-amino acids in a stereoretentive manner. This two-step sequence provides a new synthetic protocol for optically active alpha-amino acids from gaseous CO2. Furthermore, we also found that N-acyl-N,O-acetals were successfully converted into the corresponding alpha-amino acids under 1 atm of CO2 atmosphere in high yields in the presence of Mn powder, BF3-Et2O, and LiCl. The LiCl additive is necessary in order to increase the solubility and the nucleophilicity of an organomanganese intermediate.
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