European Journal of Organic Chemistry 2018-03-14

Asymmetric synthesis of new cyclic fluorinated amino‐acids

Jing Hao; Thierry Milcent; Vadim Soloshonok; Sandrine Ongeri; Benoit Crousse

Index: 10.1002/ejoc.201800255

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Abstract

Methodology for asymmetric synthesis of CF3‐β‐proline and CF3‐6‐membered cyclic amino acids has been developed starting from readily available N‐tert‐butanesulfinyl‐(3,3,3)‐trifluoroacetald‐imine. The Zn‐mediated allylation followed by the intramolecular 5‐endo‐trig cyclisation afforded the CF3‐β‐proline, whereas the CF3‐6‐membered cyclic amino acids were obtained using a ring closing metathesis protocol of CF3‐aminodienes.