Synthesis of beta-substituted alpha-amino acids with use of iridium-catalyzed asymmetric allylic substitution |
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Authors: | Kanayama Takatoshi Yoshida Kazumasa Miyabe Hideto Kimachi Tetsutaro Takemoto Yoshiji |
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Institution: | Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. |
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Abstract: | The asymmetric synthesis of beta-substituted alpha-amino acids with use of iridium-catalyzed allylic substitution was described. The Ir-catalyzed allylic substitution of diphenylimino glycinate with allylic phosphates proceeded smoothly even at 0 degrees C and gave branch products with high enantioselectivity (up to 97% ee), when chiral bidentate phosphite bearing the 2-ethylthioethyl group was employed. In addition, both diastereomers of the branch products were synthesized stereoselectively by simply switching the base employed. These methods were also applied to the asymmetric synthesis of quaternary alpha-amino acids. |
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