期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 22, 页码 6563-6567出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201803187
关键词
lactams; rotaxanes; stereoselectivity; supramolecular chemistry; template synthesis
资金
- MINECO [CTQ2017-87231-P]
- FEDER
- Fundacion Seneca-CARM [19240/PI/14]
The synthesis of optically active interlocked and non-interlocked 2-azetidinones by intramolecular cyclization of N-(alpha-methyl)benzyl fumaramide [2]rotaxanes is described. Two different strategies of asymmetric induction were tested in which the chiral group was located either proximal or distal to the reacting center of the thread. During these experiments, an interesting equilibration process inside the macrocyclic void occurred, thus leading to the cyclization through the (alpha-methyl)benzyl carbon atom and giving rise to beta-lactams, with a quaternary carbon atom, in an enantio- and diastereocontrolled manner. This cyclization also proceeds in kinetically stable chiral pseudo[2]rotaxanes, thus allowing further de threading to provide enantioenriched 3,4-disubstituted trans-2-azetidinones. The stereochemical outcomes of the cyclization inside and outside the macrocycle demonstrated noticeable
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