Seminar

Seminar

a-Functionalization of Unprotected Alicyclic Amines via Transient Imines

  • POSTED DATE : 2022-03-30
  • WRITER : 화학과
  • HIT : 190
  • DATE : 2022년 3월 31일(목) 오후 4시 30분
  • PLACE : Webex
세미나가 이번주 목요일(3월 31일) 오후 4시 30분에 개최됩니다.

많은 참여 부탁드립니다.

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제  목 : a-Functionalization of Unprotected Alicyclic Amines via Transient Imines
연  사 : 김재현 교수(중앙대학교 약학대학)

일  시 : 2022년 3월 31일(목오후 4시 30분

<Webex참여>

방번호: 170 974 2739

링크: https://skku-ict.webex.com/meet/chem

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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.