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Updated: Mar 15, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Highly diastereoselective entry into chiral spirooxindole-based 4-methyleneazetidines via formal [2+2] annulation
G Rainoldi1, M Faltracco, L Lo Presti
1Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, Milano, 20133, Italy. alessandra.silvani@unimi.it.
Abstract:
A diastereoselective, DABCO-catalyzed reaction of isatin-derived ketimines with allenoates is described. Exploiting the stereodirecting effect of the bulky tert-butanesulfinyl chiral auxiliary, the method provides an efficient access to single diastereoisomers of unprecedented spirocyclic oxindoles, bearing a 4-methyleneazetidine ring at the spiro junction. The versatility of the method is fully demonstrated by further transformations including the conversion to relevant spirocyclic oxindolo-β-lactams.
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