title: One-Pot Conversion of N-Allyl-α-cyano Esters to α-Allyl-α-cyano Lactams through a Hydrolysis/Ketene Formation/Cyclization/Claisen Rearrangement Sequence.
abstract: An intramolecular ketene aza-Claisen rearrangement is developed for the first time to enable the stereoselective synthesis of α-ally-α-cyano-lactams from N-allyl amino esters. This reaction also exhibits outstanding chemoselectivity when an unsymmetrical bis-N-allyl group is present in the starting molecule. The usefulness of this method is demonstrated by a short synthesis of optically active bicyclolactam from l-proline.
authors.affiliation: School of Pharmaceutical Engineering and Life Science, Changzhou University , 1 Middle Gehu Road, Changzhou, Jiangsu Province 213164, China.
authors.forename: Mei-Hua
authors.initials: MH
authors.lastname: Shen
authors.affiliation: School of Pharmaceutical Engineering and Life Science, Changzhou University , 1 Middle Gehu Road, Changzhou, Jiangsu Province 213164, China.
authors.forename: Mei
authors.initials: M
authors.lastname: Han
authors.affiliation: School of Pharmaceutical Engineering and Life Science, Changzhou University , 1 Middle Gehu Road, Changzhou, Jiangsu Province 213164, China.
authors.forename: Hua-Dong
authors.initials: HD
authors.lastname: Xu
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004952:Esters; D005030:Ethylenes / Q000737:chemistry; D006868:Hydrolysis; D007659:Ketones / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D004952:Esters; D005030:Ethylenes; D007659:Ketones; D007769:Lactams; D009570:Nitriles; D011392:Proline; C008223:ketene