Asymmetric Allylic Alkylation of Diverse Nitrogen-Containing Heterocycles

Significance

Asymmetric allylic substitution reactions work with a variety of carbon, oxygen, nitrogen, and sulfur nucleophiles (see Review below). However, the use of highly reactive organo-metallic reagents such as organolithiums or Grignard reagents still remains a challenge. The authors previously showed that, under certain conditions, lithiated 2-methylpyridine could participate in allylic alkylations with good yields and reactivity (B. M. Trost, D. A. Thaisrivongs J. Am. Chem. Soc. 2008, 130, 14092). In the present communication, a much wider range of nitrogen-containing heterocycles are shown to undergo similar reactivity.

Review: B. M. Trost, M. L. Crawley Chem. Rev. 2003, 103, 2921-2944.