About
Research
Academics
People
Board
많은 참여 부탁드립니다.
===============================================================================
제 목 : a-Functionalization of Unprotected Alicyclic Amines via Transient Imines
연 사 : 김재현 교수(중앙대학교 약학대학)
일 시 : 2022년 3월 31일(목) 오후 4시 30분
<Webex참여>
방번호: 170 974 2739링크: https://skku-ict.webex.com/meet/chem
================================================================================
a-Functionalization of Unprotected Alicyclic Amines via Transient Imines
Jae Hyun Kim
College of Pharmacy, Chung-Ang University, Seoul 06974, South Korea
Email: jaehyunkim@cau.ac.kr
Substituted cyclic amines are key structural motif of important pharmaceutical drugs and natural products. A new advance in the access to such heterocycles is the functionalization of transient imines which can be prepared in situ from N-lithiated cyclic amines and simple ketone oxidants. We have achieved the alkylation of transiently generated imines with enolates in the presence of Lewis acid to provide valuable β-amino ketones.[1] The resulting a-alkylated cyclic amines could be further functionalized via condensation or intramolecular heteroconjugate addition by taking advantage of the unprotected secondary amine moiety. The alkylation of transiently generated imines with β-ketoacids under mild decarboxylative conditions provided β-amino ketones with unprecedented ease.[2] Importantly, regioselective α’-alkylation was achieved for substrates with existing α-substituents. Further substrate diversification was achieved by combining decarboxylative alkylation with a subsequent SNAr step in a single operation to provide polycyclic dihydroquinolones.