title: A novel enantioselective alkylation and its application to the synthesis of an anticancer agent.
abstract: A novel enantioselective alkylation of double benzylic substrates with secondary electrophiles is reported. A simple norephedrine-based chiral ligand was synthesized that gives alkylation product in 95% yield and 95% ee. A unique water effect on the enantioselectivity was unveiled. Good to excellent ee values were obtained with a number of double benzylic substrates and secondary electrophiles. This novel reaction has been applied to the synthesis of a promising anticancer agent.
authors.affiliation: Chemical Process Research and Development, Schering-Plough Research Institute, 1011 Morris Avenue, Union, NJ 07083, USA.
authors.forename: Shen-Chun
authors.initials: SC
authors.lastname: Kuo
authors.forename: Frank
authors.initials: F
authors.lastname: Chen
authors.forename: Donald
authors.initials: D
authors.lastname: Hou
authors.forename: Agnes
authors.initials: A
authors.lastname: Kim-Meade
authors.forename: Charles
authors.initials: C
authors.lastname: Bernard
authors.forename: Jinchu
authors.initials: J
authors.lastname: Liu
authors.forename: Stacy
authors.initials: S
authors.lastname: Levy
authors.forename: George G
authors.initials: GG
authors.lastname: Wu
mesh_terms: D000478:Alkylation; D000970:Antineoplastic Agents / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D015394:Molecular Structure; D010880:Piperidines / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D011725:Pyridines / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism; D003986:Dibenzocycloheptenes
chemical_list: D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D010880:Piperidines; D011725:Pyridines; C115354:lonafarnib; D003986:Dibenzocycloheptenes