Studies toward gymnodimine: development of a single-pot Hua reaction for the synthesis of highly hindered cyclic imines |
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Authors: | Ahn Y Cardenas G I Yang J Romo D |
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Institution: | Department of Chemistry, P.O. Box 30012, Texas A&M University, College Station, Texas 77842-3012, USA. |
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Abstract: | 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. |
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