Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 6, Pages 1642-1648Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo01927a
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- National Natural Science Foundation of China [21772043]
- Shanghai Pujiang Program [19PJ1403000]
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A KOtBu-catalyzed alpha-homoallylic alkylation of lactams with 1,3-dienes is reported in this study. This transition metal-free and atom-economical protocol allows for the formation of alpha-homoallylic alkylated lactams bearing alpha-quaternary carbon centers with excellent regioselectivity. A proposed cation-pi interaction between the in situ-generated potassium enolate and the diene plays a key role in accelerating this transformation.
We report a KOtBu-catalyzed alpha-homoallylic alkylation of lactams with 1,3-dienes. With this transition metal-free and atom-economical protocol, a variety of alpha-homoallylic alkylated lactams bearing alpha-quaternary carbon centers were formed in a 2,1-addition manner with excellent regioselectivity. A cation-pi interaction between the in situ-generated potassium enolate and the diene is proposed to play a key role in accelerating this transformation.
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