Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of N-Aryl Pyrrolidines

  • Jo, Hanbyeol; 
  • Hassan, Ahmed H. E.; 
  • Jung, Seung Young; 
  • Lee, Jae Kyun; 
  • Cho, Yong Seo; 
  • ... Min, Sun-Joon
Citations

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30
Citations

SCOPUS

31

초록

A concise synthesis of 8-azabicyclo [3.2.1] octanes via sequential oxidative Mannich reactions is described. This approach involves an intermolecular oxidative Mannich coupling reaction between N-aryl pyrrolidines with TMS enol ether and a subsequent intramolecular oxidative Mannich cyclization of the corresponding silyl enol ether. DDQ is used as a key oxidant for both reactions.

키워드

CATALYTIC ENANTIOSELECTIVE SYNTHESIS; DEHYDROGENATIVE COUPLING REACTIONS; BOND-FORMING REACTIONS; C-H FUNCTIONALIZATION; TROPANE ALKALOIDS; ASYMMETRIC-SYNTHESIS; TERTIARY-AMINES; AEROBIC CONDITIONS; DERIVATIVES; PHOTOREDOX; CATALYTIC ENANTIOSELECTIVE SYNTHESIS; DEHYDROGENATIVE COUPLING REACTIONS; TROPANE ALKALOIDS; C-C; ASYMMETRIC-SYNTHESIS; BOND FORMATION; FUNCTIONALIZED TROPANES; PHOTOREDOX; AMINES; DERIVATIVES
제목
Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of N-Aryl Pyrrolidines
저자
Jo, Hanbyeol; Hassan, Ahmed H. E.; Jung, Seung Young; Lee, Jae Kyun; Cho, Yong Seo; Min, Sun-Joon
DOI
10.1021/acs.orglett.8b00098
발행일
2018-02
유형
Article
저널명
Organic Letters
권
20
호
4
페이지
1175 ~ 1178