Diastereoselective Access to Tri‐ and Pentacyclic Spiro‐γ‐lactam‐oxindole Cores through a Tandem Aza‐Michael Initiated Ring Closure Sequence
Identifieur interne : 000837 ( Main/Exploration ); précédent : 000836; suivant : 000838Diastereoselective Access to Tri‐ and Pentacyclic Spiro‐γ‐lactam‐oxindole Cores through a Tandem Aza‐Michael Initiated Ring Closure Sequence
Auteurs : Iyad Allous [Syrie] ; Sébastien Comesse [France] ; Morgane Sanselme [France] ; Adam DaïchSource :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2011-09.
English descriptors
Abstract
Herein, we present a new development of the previously described aza‐Michael‐initiated ring closure (MIRC) process to access spirooxindole cores. The key spiro‐cyclization step between various α‐bromoacetamides and methyleneindolinones was efficient and tolerant of a wide range of functional groups. Yields and diastereoselectivities for the spirocyclization were usually high and furnished original spiro[oxindole‐3,3′‐γ‐lactam] derivatives. The utility of these novel building blocks for the preparation of more sophisticated derivatives was demonstrated by the preparation of four pentacyclic spirooxindoles.
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DOI: 10.1002/ejoc.201100731
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