Asymmetric synthesis of aldehydes via alkylation of lithiated chiral α-phenethylimines

✍ Scribed by Robert R. Fraser; Fuminori Akiyama; Jacques Banville

• Book ID: 104237879
• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 371 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)86467-4

✦ Synopsis

The lithiation and alkylation of three aldehydes in the form of their a-phenethylimines has been shown to yield chiral a-alkvlaldehydes of 67-70% optical purity. We recently observed some unusual stereochemical preferences associated with lithiated ketimines (1) and aldimines (2). Both carbonyl derivatives underwent lithiation alpha to the "carbonyl" carbon to give exclusively the m derivative, which, in the case of cyclohexanone imines, gave axial substitution only. In the recent past, the use of imines in asymmetric synthesis has been elegantly demonstrated by the work of Meyers (3). Cyclic