A novel enantioselective alkylation and its application to the synthesis of an anticancer agent.
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.
Kuo
Shen-Chun
SC
Chemical Process Research and Development, Schering-Plough Research Institute, 1011 Morris Avenue, Union, NJ 07083, USA.
Chen
Frank
F
Hou
Donald
D
Kim-Meade
Agnes
A
Bernard
Charles
C
Liu
Jinchu
J
Levy
Stacy
S
Wu
George G
GG
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
D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D010880:Piperidines; D011725:Pyridines; C115354:lonafarnib; D003986:Dibenzocycloheptenes