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Rhodium-catalyzed Reformatsky-type reaction for asymmetric synthesis of difluoro-β-lactams using menthyl group as a chiral auxiliary |
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| Authors: | Atsushi Tarui Daiki Ozaki Naoko Nakajima Yuto Yokota Yasser S. Sokeirik Kazuyuki Sato Masaaki Omote Itsumaro Kumadaki Akira Ando |
| Affiliation: | aFaculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan |
| Abstract: | We developed a new methodology for the asymmetric Reformatsky-type reaction of (−)-menthyl bromodifluoroacetate (2) with imine in the presence of RhCl(PPh3)3. Ester 2 with the cost-effective chiral auxiliary gave (S)-difluoro-β-lactams in moderate to good yields and high diastereoselectivities through spontaneous removal of the auxiliary. |
| Keywords: | Fluorine Rhodium Difluoro-β-lactam Imine Diethylzinc Chiral auxiliary Reformatsky-type reaction |
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