Ring transformation of 2-(haloalkyl)azetidines into 3,4-disubstituted pyrrolidines and piperidines

Organic Letters
Willem Van BrabandtNorbert De Kimpe

Abstract

[reaction: see text] Reduction of 4-(haloalkyl)azetidin-2-ones with chloroalane (AlH(2)Cl) afforded new 2-(haloalkyl)azetidines in high yields. The latter compounds proved to be very useful starting materials for rearrangements toward stereospecifically defined five- and six-membered azaheterocycles, such as 3,4-cis-disubstituted pyrrolidines and piperidines. During these reactions, bicyclic azetidinium intermediates were formed which were ring opened by a variety of nucleophiles. Hereby, reactions proceeding via 1-azoniabicyclo[2.2.0]hexanes are reported for the first time.

References

Jan 1, 1999·Bioorganic & Medicinal Chemistry Letters·M BouyguesJ L Kraus
Nov 10, 2000·Natural Product Reports·D O'Hagan
Apr 2, 2002·The Journal of Organic Chemistry·Yves DejaegherNorbert De Kimpe
Apr 23, 2005·The Journal of Organic Chemistry·Willem Van Brabandt, Norbert De Kimpe

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Citations

Dec 25, 2012·Tetrahedron·Anushree Kamath, Iwao Ojima
Jan 14, 2012·The Journal of Organic Chemistry·Scott W BagleyScott J Bader
Oct 14, 2014·The Journal of Organic Chemistry·Gong-Qing Liu, Yue-Ming Li
Jun 12, 2008·Chemistry : a European Journal·Matthias D'hoogheNorbert De Kimpe
Jan 12, 2010·Chemistry, an Asian Journal·Shingo HataMakoto Shimizu
Dec 17, 2008·Organic & Biomolecular Chemistry·Matthias D'hoogheNorbert De Kimpe
Sep 7, 2011·Chemical Society Reviews·Sonja StankovićHyun-Joon Ha
Jul 12, 2016·The Journal of Organic Chemistry·Bruno DrouillatFrançois Couty
May 17, 2017·Angewandte Chemie·Alexander A KirichokPavel K Mykhailiuk
Jan 18, 2018·Chemistry : a European Journal·Alexander A KirichokPavel K Mykhailiuk
Sep 11, 2008·Chemical Reviews·Alberto BrandiFranca M Cordero
Nov 18, 2009·The Journal of Organic Chemistry·Biswanath DasGandolla Chinna Reddy
Jun 30, 2021·Archiv der Pharmazie·Deepa R ParmarAnand G Vala
Oct 12, 2010·The Journal of Organic Chemistry·Manas K GhoraiRaj Kumar Das
Jan 18, 2018·ACS Omega·Ngangbam Renubala DeviAnil K Saikia

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