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Studies toward Gymnodimine:  Development of a Single-Pot Hua Reaction for the Synthesis of Highly Hindered Cyclic Imines

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journal contribution
posted on 06.02.2001, 00:00 by Yong Ahn, Gabriela I. Cardenas, Ju Yang, Daniel Romo
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 α,α-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.