Synthesis of azaspiro[4.5]decane systems by oxidative cyclization of olefinic precursors

Add time:07/25/2019    Source:sciencedirect.com

The synthesis of 6-benzyloxycarbonyl-1-oxa-6-azaspiro[4.5]decan-2-one (17) and 6-benzyloxycarbonyl-1,6-diazaspiro[4.5]decan-2-one (18) from the D,L-pipecolic acid derivative 10, is described. The synthesis of (±)-6-benzyl-3-methyl-1,6-diazaspiro[4.5]dec-3-ene-2,7-dione (29), the spiro structural unit of (±)-pandamarine (8) has been achieved by oxidative cylization of the (Z) and (E) isomers of 5-(N-benzyl-4-carboxamidobutylidene)-3-methyl-3-pyrrolin-2-one (25) and (26). The stereoselectivity obtained in the intramolecular cyclization process has also been discussed.

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