The efficient desymmetrization of N-(2-tert-butylphenyl)maleimides was realized by means of a Michael addition reaction of a series of carbon nucleophiles generating the corresponding axially chiral succinimides in high yields. The use of (DHQD)2Pyr as catalyst was fundamental to achieve the remote control of the stereogenic chiral axis with the concurrent construction of adjacent quaternary and tertiary stereocenters.
Targeting remote axial chirality control of N-(2-tert-butylphenyl)succinimides by means of Michael addition type reactions / Di Iorio, Nicola; Champavert, Florian; Erice, Agostino; Righi, Paolo; Mazzanti, Andrea; Bencivenni, Giorgio. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 72:(2016), pp. 5191-5201. [10.1016/j.tet.2016.02.052]
Targeting remote axial chirality control of N-(2-tert-butylphenyl)succinimides by means of Michael addition type reactions
DI IORIO, NICOLA;RIGHI, PAOLO;MAZZANTI, ANDREA;BENCIVENNI, GIORGIO
2016
Abstract
The efficient desymmetrization of N-(2-tert-butylphenyl)maleimides was realized by means of a Michael addition reaction of a series of carbon nucleophiles generating the corresponding axially chiral succinimides in high yields. The use of (DHQD)2Pyr as catalyst was fundamental to achieve the remote control of the stereogenic chiral axis with the concurrent construction of adjacent quaternary and tertiary stereocenters.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
