Dramatic Effect of γ‑Heteroatom Dienolate Substituents on Counterion Assisted Asymmetric Anionic Amino-Cope Reaction Cascades

• Published in: Journal of the American Chemical Society Vol. 143; no. 15; pp. 5793 - 5804
• Main Authors: Das, Pradipta, Delost, Michael D, Qureshi, Munaum H, Bao, Jianhua, Fell, Jason S, Houk, Kendall N, Njardarson, Jon T
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 21.04.2021; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; REARRANGEMENTS; INDUCTION

We report a dramatic effect on product outcomes of the lithium ion enabled amino-Cope-like anionic asymmetric cascade when different γ-dienolate heteroatom substituents are employed. For dienolates with azide, thiomethyl, and trifluoromethylthiol substituents, a Mannich/amino-Cope/cyclization cascad...