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Diastereoselective Access to Tri‐ and Pentacyclic Spiro‐γ‐lactam‐oxindole Cores through a Tandem Aza‐Michael Initiated Ring Closure Sequence
Author(s) -
Allous Iyad,
Comesse Sébastien,
Sanselme Morgane,
Daïch Adam
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100731
Subject(s) - oxindole , chemistry , tandem , michael reaction , lactam , ring (chemistry) , closure (psychology) , sequence (biology) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , materials science , economics , market economy , composite material
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.