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

详细信息    查看全文

• 作者：Bastien Chatelet ; Lionel Joucla ; Daniele Padula ; Lorenzo Di Bari ; Guillaume Pilet ; Vincent Robert ; V茅ronique Dufaud ; Jean-Pierre Dutasta ; Alexandre Martinez
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：February 6, 2015
• 年：2015
• 卷：17
• 期：3
• 页码：500-503
• 全文大小：281K
• ISSN：1523-7052

文摘

Enantiopure hemicryptophanes designed from the cyclotriveratrylene (CTV) unit display remarkable properties in selective host鈥揼uest 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 脜, 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.