Practical and divergent synthesis of 1- and 5-substituted 3,9-diazaspiro[5.5]undecanes and undecan-2-ones

A divergent synthesis of 1- and 5-substituted 3,9-diazaspiro[5.5]undecanes and undecan-2-ones is described, in which the key step is an efficient Michael addition of a lithium enolate to a tetrasubstituted olefin acceptor. A variety of substituents (butyl, phenyl, and propoxyl) were introduced at C-...

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Bibliographic Details
Published in:Tetrahedron letters 2008-10, Vol.49 (44), p.6371-6374
Main Authors: Yang, Hanbiao, Lin, Xiao-Fa, Padilla, Fernando, Rotstein, David M.
Format: Article
Language:English
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Summary:A divergent synthesis of 1- and 5-substituted 3,9-diazaspiro[5.5]undecanes and undecan-2-ones is described, in which the key step is an efficient Michael addition of a lithium enolate to a tetrasubstituted olefin acceptor. A variety of substituents (butyl, phenyl, and propoxyl) were introduced at C-1(5) in this manner. In addition, an asymmetric synthesis of one member of this series was achieved using an Evans oxazolidinone chiral auxiliary reagent.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.08.086