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- Title
Organocatalytic Enantioselective Synthesis of Seven‐Membered Ring with Inherent Chirality.
- Authors
Li, Jia‐Hao; Li, Xiao‐Kai; Feng, Jia; Yao, Wang; Zhang, Huan; Lu, Chuan‐Jun; Liu, Ren‐Rong
- Abstract
Inherent chirality is used to describe chiral cyclic molecules devoid of central, axial, planar, or helical chirality and has tremendous applications in chiral recognition and enantioselective synthesis. Catalytic and divergent syntheses of inherently chiral molecules have attracted increasing interest from chemists. Herein, we report the enantioselective synthesis of inherently chiral tribenzocycloheptene derivatives via chiral phosphoric acid (CPA)‐catalyzed condensation of cyclic ketones and hydroxylamines. This chemistry paves the way to accessing the less stable derivatives of 7‐membered rings with inherent chirality. A series of chiral tribenzocycloheptene oxime ethers was synthesized in good yields (up to 97 %) with excellent enantioselectivities (up to 99 % ee).
- Subjects
CHIRALITY; CHIRAL recognition; PHOSPHORIC acid; CHEMISTS; CONDENSATION; KETONES
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 8, p1
- ISSN
0044-8249
- Publication type
Academic Journal
- DOI
10.1002/ange.202319289