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

Title
Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of N-Aryl Pyrrolidines
Author
민선준
Keywords
CATALYTIC ENANTIOSELECTIVE SYNTHESIS; DEHYDROGENATIVE COUPLING REACTIONS; BOND-FORMING REACTIONS; C-H FUNCTIONALIZATION; TROPANE ALKALOIDS; ASYMMETRIC-SYNTHESIS; TERTIARY-AMINES; AEROBIC CONDITIONS; DERIVATIVES; PHOTOREDOX
Issue Date
2018-02
Publisher
AMER CHEMICAL SOC
Citation
ORGANIC LETTERS, v. 20, No. 4, Page. 1175-1178
Abstract
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.
URI
https://pubs.acs.org/doi/10.1021/acs.orglett.8b00098http://repository.hanyang.ac.kr/handle/20.500.11754/105362
ISSN
1523-7060
DOI
10.1021/acs.orglett.8b00098
Appears in Collections:
COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY[E](과학기술융합대학) > CHEMICAL AND MOLECULAR ENGINEERING(화학분자공학과) > Articles
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