Studies toward gymnodimine: development of a single-pot Hua reaction for the synthesis of highly hindered cyclic imines.
[structure: see text]. In studies directed toward gymnodimine and related marine toxins, a single-pot variation of the Hua cyclic imine synthesis has been developed. The reaction involves generation of N-trimethylsilyl lactams in situ followed by alkyllithium addition leading directly to cyclic imines. Importantly, this reaction proceeds efficiently with highly hindered alpha,alpha-dialkyl lactams, provided 1,2-dimethoxyethane (DME) is used as solvent, leading to stable cyclic imines. Overall, this transformation allows a one-pot coupling of an alkyliodide and a lactam to give a cyclic imine.
Ahn
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Department of Chemistry, P.O. Box 30012, Texas A&M University, College Station, Texas 77842-3012, USA.
Cardenas
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Yang
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Romo
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D000818:Animals; D003500:Cyclization; D004141:Dinoflagellida; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D006844:Hydrocarbons, Cyclic; D007097:Imines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008387:Marine Toxins / Q000138:chemical synthesis*; D013696:Temperature
D006575:Heterocyclic Compounds, 3-Ring; D006844:Hydrocarbons, Cyclic; D007097:Imines; D007202:Indicators and Reagents; D008387:Marine Toxins; C407350:gymnodimine