Complexity-generating tandem Petasis 3-component/intramolecular Diels–Alder and ROM–RCM reactions for the diastereoselective synthesis of sp3-rich heterocyclic compound libraries are presented.
The Ritter‐type reaction of arylnitriles and N‐acyliminium ions, generated in situ from dihydroxy‐γ‐lactams gives tetrahydropyrrolooxazolones in excellent yields.
Reductive Cyclization and Petasis-Like Reaction for the Synthesis of Functionalized -Lactams. -N-substituted ,-dihydroxy--lactams are convenient substrates for Petasis-like reactions with boronic acids. Both electron-rich and electron-deficient boronic acids are employed for nucleophilic additions to cyclic N-acyliminium ions derived from the dihydroxylactams. cis-Diastereoselectivity is observed with electron--deficient boronic acids, while electron-rich boronic acids show no or poor selectivity. This is explained by chelation-controlled vs. direct addition of the boronic acids to the N-acyliminium ions. -(WU, P.; PETERSEN, M. A.; COHRT, A. E.; PETERSEN, R.; CLAUSEN*, M. H.; NIELSEN, T. E.; Eur.
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