Abstract
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.
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