Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction
Straminelli, L., Vicentini, F., Di Sabato, A., Montone, C. M., Cavaliere, C., Rissanen, K., Leonelli, F., & Vetica, F. (2022). Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction. Journal of Organic Chemistry, 87(15), 10454-10461. https://doi.org/10.1021/acs.joc.2c01046
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Journal of Organic ChemistryDate
2022Copyright
© 2022 The Authors. Published by American Chemical Society
A highly stereoselective procedure for the synthesis of spiro-polycyclic oxindoles bearing five contiguous stereogenic centers including two tetrasubstituted carbons has been developed. Under sequential organocatalysis performed by a pyrrolidine-based organocatalyst and DBU, a highly atom-economical Michael–domino Michael/aldol reaction sequence was optimized, yielding variously functionalized spiro-decalin oxindoles with excellent stereoselectivity (>99:1 dr, up to 92% ee).
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The authors gratefully thank the colleagues at Sapienza University of Rome (Prof. Patrizia Gentili, Prof. Marta Feroci, Prof. Marco Bella), Dr. Giuliana Righi, and the Institute of Biological Systems (ISB) of the Italian National Research Council (CNR) for the donation of chemicals. Financial support from Sapienza University of Rome (Grant Number RP12117A5C0CA0CC) is gratefully acknowledged.License
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