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Highly enantioselective phase‐transfer catalytic α‐alkylation of α‐tert‐butoxycarbonyllactams: Construction of β‐quaternary chiral pyrrolidine and piperidine systems : Highly enantioselective phase-transfer catalytic alpha-alkylation of alpha-tert-butoxycarbonyllactams: Construction of beta-quaternary chiral pyrrolidine and piperidine systems

Cited 17 time in Web of Science Cited 17 time in Scopus
Authors

Park, Yohan; Lee, Young Ju; Hong, Suck Chang; Kim, Mi-hyun; Lee, Myungmo; Kim, Taek-Soo; Lee, Jae Kyun; Jew, Sang-sup; Park, Hyeung-geun

Issue Date
2011-12
Publisher
John Wiley & Sons Ltd.
Citation
Advanced Synthesis and Catalysis, Vol.353 No.18, pp.3313-3318
Abstract
A new enantioselective alpha-alkylation of alpha-tert-butoxycarbonyllactams for the construction of beta-quaternary chiral pyrrolidine and piperidine core systems is reported. alpha-Alkylations of N-methyl-alpha-tert-butoxycarbonylbutyrolactam and N-diphenylmethyl-alpha-tert-butoxycarbonylvalerolactam under phase-transfer catalytic conditions (solid potassium hydroxide, toluene, -40 degrees C) in the presence of (S,S)-3,4,5-trifluorophenyl-3,3',5,5'-tetrahydro-2,6-bis(3,4,5-trifluorophenyl)-4,4'-spirobi[4H-dinaphth[2,1-c:1',2'-e]azepinium] bromide [(S,S)-NAS Br] (5 mol%) afforded the corresponding alpha-alkyl-alpha-tert-butoxycarbonyllactams in very high chemical (up to 99%) and optical yields (up to 98% ee). Our new catalytic systems provide attractive synthetic methods for pyrrolidine- and piperidine-based alkaloids and chiral intermediates with beta-quaternary carbon centers.
ISSN
1615-4150
URI
https://hdl.handle.net/10371/202033
DOI
https://doi.org/10.1002/adsc.201100542
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  • College of Pharmacy
  • Department of Manufacturing Pharmacy
Research Area Development of methodologies using metal catalyst, Total synthesis of natural products

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