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Memory of Chirality in Bromoalkyne Carbocyclization: Applications in Asymmetric Total Synthesis of Hasubanan Alkaloids

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journal contribution
posted on 14.12.2018, 16:04 by Shenpeng Tan, Feng Li, Soojun Park, Sanghee Kim
A transition-metal-free 5-exo-dig asymmetric cyclization of α-amino ester enolates onto bromoalkynes provided a product with excellent enantioselectivity via the memory of chirality concept. This strategy was applied to a concise total synthesis of (−)-runanine and a formal synthesis of (−)-8-demethoxyrunanine and (−)-cepharatine D.