Synthesis 2017; 49(07): 1519-1530
DOI: 10.1055/s-0036-1588408
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© Georg Thieme Verlag Stuttgart · New York

Michael Addition of Oxindoles to N-(2-tert-Butylphenyl)maleimides: Efficient Desymmetrization for the Synthesis of Atropisomeric Succinimides with Quaternary and Tertiary Stereocenters

Nicola Di Iorio
Department of Industrial Chemistry ‘Toso Montanari’, School of Science, University of Bologna, viale del Risorgimento 4, 40136 Bologna, Italy   eMail: [email protected]
,
Lorenzo Soprani
Department of Industrial Chemistry ‘Toso Montanari’, School of Science, University of Bologna, viale del Risorgimento 4, 40136 Bologna, Italy   eMail: [email protected]
,
Simone Crotti
Department of Industrial Chemistry ‘Toso Montanari’, School of Science, University of Bologna, viale del Risorgimento 4, 40136 Bologna, Italy   eMail: [email protected]
,
Emanuela Marotta
Department of Industrial Chemistry ‘Toso Montanari’, School of Science, University of Bologna, viale del Risorgimento 4, 40136 Bologna, Italy   eMail: [email protected]
,
Andrea Mazzanti
Department of Industrial Chemistry ‘Toso Montanari’, School of Science, University of Bologna, viale del Risorgimento 4, 40136 Bologna, Italy   eMail: [email protected]
,
Paolo Righi
Department of Industrial Chemistry ‘Toso Montanari’, School of Science, University of Bologna, viale del Risorgimento 4, 40136 Bologna, Italy   eMail: [email protected]
,
Giorgio Bencivenni*
Department of Industrial Chemistry ‘Toso Montanari’, School of Science, University of Bologna, viale del Risorgimento 4, 40136 Bologna, Italy   eMail: [email protected]
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Publikationsverlauf

Received: 11. Januar 2017

Accepted after revision: 13. Januar 2017

Publikationsdatum:
08. Februar 2017 (online)


Abstract

The desymmetrization of N-(2-tert-butylphenyl)maleimides was realized by means of a Michael reaction of N-(tert-butoxycarbonyl)-3-phenyloxindoles leading to the corresponding axially chiral succinimides in high yields. The use of a squaramide cinchonidine organocatalyst was fundamental to achieve the simultaneous remote control of the stereogenic axis and adjacent quaternary and tertiary stereocenters.

Supporting Information

 
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