Remote Control of Helical Chirality: Thermodynamic Resolution of a Racemic Mixture of CTV Units by Remote Stereogenic Centers

Bastien Chatelet (1) , Lionel Joucla (1) , Daniele Padula (2) , Lorenzo Di Bari (3) , Guillaume Pilet (4) , Vincent Robert (5) , Véronique Dufaud (6) , Jean-Pierre Dutasta (1) , Alexandre Martinez (1, 7)

1 LC - Laboratoire de Chimie - UMR5182
2 IOCB / CAS - Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences
3 Dipartimento di Chimica e Chimica Industriale
4 LMI - Laboratoire des Multimatériaux et Interfaces
5 Institut de Chimie de Strasbourg
6 C2P2 - Laboratoire de Chimie, Catalyse, Polymères et Procédés, R 5265
7 ISM2 - Institut des Sciences Moléculaires de Marseille

Enantiopure hemicryptophanes designed from the cyclotriveratrylene (CTV) unit display remarkable properties in selective host–guest recognition or as supramolecular catalysts. The unprecedented control of the helical chirality of the CTV unit by remote stereogenic centers of a tren moiety is reported, providing an original access to this highly promising class of host molecules. Although the chiral centers and the CTV unit are separated by more than 10 Å, one single diastereomer is formed; the nature of the diastereoselective process is discussed and the procedure is exemplified using different enantiopure tren derivatives. This work also highlights the influence of the chirality of the CTV unit on the whole cage structure.

Domaines: Chimie théorique et/ou physique

Bastien Chatelet, Lionel Joucla, Daniele Padula, Lorenzo Di Bari, Guillaume Pilet, et al.. Remote Control of Helical Chirality: Thermodynamic Resolution of a Racemic Mixture of CTV Units by Remote Stereogenic Centers. Organic Letters, 2015, 17 (3), pp.500-503. ⟨10.1021/ol5035194⟩. ⟨hal-01234191⟩