Synthesis 2013; 45(2): 225-230
DOI: 10.1055/s-0032-1316831
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Isomeric 6-Trifluoromethyl-3-azabicyclo[3.1.0]hexanes: Conformationally Restricted Analogues of 4-Trifluoromethylpiperidine

Olexiy S. Artamonov
a  Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, Kyiv-94 02660, Ukraine
,
Evgeniy Y. Slobodyanyuk
b  Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine    Email: Pavel.Mykhailiuk@gmail.com
c  Department of Chemistry, and Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, Kyiv 01033, Ukraine
,
Oleg V. Shishkin
d  STC, ‘Institute for Single Crystals,’ National Academy of Science, 60 Lenina ave., Kharkiv 61001, Ukraine
,
Igor V. Komarov
b  Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine    Email: Pavel.Mykhailiuk@gmail.com
c  Department of Chemistry, and Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, Kyiv 01033, Ukraine
,
Pavel K. Mykhailiuk*
b  Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine    Email: Pavel.Mykhailiuk@gmail.com
c  Department of Chemistry, and Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, Kyiv 01033, Ukraine
› Author Affiliations
Further Information

Publication History

Received: 02 November 2012

Accepted after revision: 29 November 2012

Publication Date:
18 December 2012 (eFirst)

Abstract

Two isomeric conformationally restricted analogues of 4-trifluoromethylpiperidine were designed. The synthesis was performed in four steps from commercially available N-benzylmaleimide. The key reaction was the [3+2] cycloaddition between trifluoromethyldiazomethane and N-benzylmaleimide.

Supporting Information

 
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