Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 7, Pages 1318-1327Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101529
Keywords
Spiro compounds; Nitrogen heterocycles; Organocatalysis; Enantio-selectivity; Michael addition
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Funding
- National Natural Science Foundation of China (NSFC) [21072145]
- Foundation for the Authors of National Excellent Doctoral Dissertations of PR China [200931]
- Natural Science Foundation of Jiangsu Province of China [BK2009115]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
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The asymmetric catalytic synthesis of naturally occurring and biologically active spiro compounds is a challenge for modern chemical methodology. Here we report the construction of spiro compounds through cascade [5+1] double Michael reactions between divinyl ketones and N-unprotectedoxindoles or N-phenyl-protected pyrazolones catalyzed by a combination of the easily available 9-amino-9-deoxy-epi-quinine with N-Boc-D-phenylglycine. The desired multistereogenic spiro[cyclohexanone-oxindoles and -pyrazolones] were obtained with high yields (up to 98?%) andstereoselectivities (up to >20:1 dr, 99?% ee).
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