Mechanistic insight into the spirocyclopropane isoxazolidine ring contraction.
A mechanistic study of the ring contraction of spirocyclopropane isoxazolidines to form β-lactams is reported. Based on experimental and computational investigations, we propose a concerted mechanism that proceeds with retention of configuration during cyclopropane cleavage.
Laboratorium für Organische Chemie, ETH Zürich, HCI H335 , Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland.
Stefan
S
Diethelm
Franziska
F
Schoenebeck
Erick M
EM
Carreira
D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D011789:Quantum Theory; D013141:Spiro Compounds / Q000737:chemistry*; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
D003521:Cyclopropanes; D010080:Oxazoles; D013141:Spiro Compounds; D047090:beta-Lactams; C064210:oxazolidine; C030797:cyclopropane