Organic base-catalyzed stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids |
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| Authors: | Shibata Norio Nishimine Takayuki Shibata Naoyuki Tokunaga Etsuko Kawada Kosuke Kagawa Takumi Sorochinsky Alexander E Soloshonok Vadim A |
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| Affiliation: | Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan. nozshiba@nitech.ac.jp |
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| Abstract: | Organic base-catalyzed reaction of (S)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine with dialkyl malonates was found to be effective for synthesis of both (S,S(S)) and (R,S(S)) β-aminomalonates in high yield with good to excellent diastereoselectivity (76-98% de). The products of this Mannich reaction provide direct access to β-trifluoromethyl-β-alanine of either (R) or (S) absolute configuration. |
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