PMID: 11929246Apr 4, 2002Paper

Catalytic regioselective sulfonylation of alpha-chelatable alcohols: scope and mechanistic insight

Journal of the American Chemical Society
Michael J MartinelliBerta Kosmrlj

Abstract

This paper describes a convenient protocol for the regioselective sulfonylation of alpha-chelatable alcohols. Typically, the reaction of alpha-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et(3)N in the presence of 2 mol % of Bu(2)SnO leads to rapid, regioselective, and exclusive monotosylation. The pK(a) of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of (119)Sn NMR studies.

References

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Citations

Jan 31, 2012·The Journal of Organic Chemistry·Hai DongOlof Ramström
Mar 15, 2013·The Journal of Organic Chemistry·Li Xia, Todd L Lowary
Jan 1, 2009·Beilstein Journal of Organic Chemistry·Vincent A BrunetDavid O'Hagan
Feb 3, 2016·Chemical & Pharmaceutical Bulletin·Tomoya FujiwaraTakayuki Yakura
Feb 10, 2016·Journal of the American Chemical Society·Guillaume PelletierScott J Miller
Nov 19, 2015·Carbohydrate Research·Karin ThorsheimUlf Ellervik
Apr 5, 2016·Chemical & Pharmaceutical Bulletin·Bo LiuTakayuki Yakura
Nov 17, 2015·Chemical Communications : Chem Comm·Manuel Jäger, Adriaan J Minnaard
Nov 11, 2017·Angewandte Chemie·Weidong ShangDawen Niu
Jan 14, 2011·Nature·Daniel M RosenbaumBrian K Kobilka
Feb 18, 2014·Natural Product Reports·Charlélie BensoussanJanine Cossy
Sep 7, 2019·Angewandte Chemie·Hui Yang, Wen-Hua Zheng
Dec 28, 2010·Organic & Biomolecular Chemistry·Oskari K Karjalainen, Ari M P Koskinen
Jul 24, 2013·Organic & Biomolecular Chemistry·Doris Lee, Mark S Taylor
Mar 14, 2014·Chemistry : a European Journal·I-Hon ChenVy M Dong
Oct 11, 2008·Organic Letters·Yosuke DemizuOsamu Onomura
Apr 23, 2008·Organic Letters·Barry M Trost, Brandon L Ashfeld
Aug 19, 2008·The Journal of Organic Chemistry·Zhi-Bin ZhenYikang Wu
Oct 27, 2010·Organic Letters·Annika Gille, Martin Hiersemann
Mar 2, 2011·Journal of the American Chemical Society·Doris Lee, Mark S Taylor
Jun 6, 2018·Chemical Reviews·Suvarn S KulkarniShang-Cheng Hung
Feb 11, 2015·The Journal of Organic Chemistry·Simiao LuT Bruce Grindley
Dec 7, 2018·Chemical Reviews·Victoria Dimakos, Mark S Taylor
May 3, 2019·Journal of Medicinal Chemistry·Markus StanekPeter Gmeiner
Jul 18, 2006·Chemical Research in Toxicology·Priscilla H FernandesR Stephen Lloyd
Jun 11, 2009·Carbohydrate Research·Subramanian DevarajMysore S Shashidhar

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