Unexpected highly chemoselective deprotection of the acetals from aldehydes and not ketones: TESOTf-2,6-lutidine combination

Journal of the American Chemical Society
Hiromichi FujiokaYasuyuki Kita

Abstract

Acetal functions are recognized as good protecting groups of carbonyl groups. Although many deprotecting methods of acetals to carbonyl functions have already been developed, there is no methodology which can deprotect acetals in the presence of ketals because the usual acidic or radical reactions occur more easily via the more stable cationic or radical intermediates from the ketals. On the other hand, this new method can proceed in a reverse manner to that described in previous reports. That is, the method can deprotect aliphatic acetals in the presence of ketals. The reaction condition is common for silylation, i.e., the TESOTf-2,6-lutidine combinations. Although the TMSOTf-2,6-lutidine combination can also deprotect acetals, it lacks chemoselectivity in deprotection of the acetals from aldehydes and ketones. The treatment of acetals with TESOTf and 2,6-lutidine in CH2Cl2 followed by a H2O workup gave the corresponding aldehydes. Of course, the compounds, which have both acetal and hydroxyl functions afforded the compounds obtained by the usual silylation of an alcohol and deprotection of an acetal without any problem. However, deprotection of the ketals from ketones was not observed during the conversion reaction of acetals...Continue Reading

References

Jul 30, 2004·Journal of the American Chemical Society·Timothy B DurhamWilliam R Roush

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Citations

Sep 9, 2005·Organic Letters·Noriaki ItagakiYoshiharu Iwabuchi
Mar 15, 2011·Organic Letters·Pushparathinam GopinathKannoth Manheri Muraleedharan
May 8, 2010·Chemical Communications : Chem Comm·Hiromichi FujiokaTomohiro Maegawa
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Damien ThevenetHelen Stoeckli-Evans
Jan 7, 2014·Chemical & Pharmaceutical Bulletin·Kenzo Yahata, Hiromichi Fujioka
Nov 12, 2015·Organic Letters·Jorin HoogenboomTom Wennekes
Nov 5, 2016·Organic Letters·Naoki YasukawaYoshinari Sawama
Jan 5, 2017·Chemical & Pharmaceutical Bulletin·Reiya Ohta, Hiromichi Fujioka
May 29, 2012·Chemistry, an Asian Journal·Hiromichi FujiokaKenichi Murai
Aug 20, 2016·Nature Communications·Roman LagoutteNicolas Winssinger
Oct 2, 2007·Chemistry : a European Journal·Hiromichi FujiokaYasuyuki Kita
Nov 2, 2017·The Journal of Antibiotics·Roman LagoutteNicolas Winssinger
Oct 2, 2020·Chemical & Pharmaceutical Bulletin·Hiromichi Fujioka
Jul 26, 2012·Chemistry : a European Journal·Akihiro GotoHiromichi Fujioka
Jun 30, 2011·Organic & Biomolecular Chemistry·Tomohiro MaegawaHiromichi Fujioka
Nov 7, 2015·Chemistry : a European Journal·Igor V PimkovPartha Basu
Dec 16, 2017·Chemical Communications : Chem Comm·Takahiro KawajiriYoshinari Sawama
Oct 14, 2009·Organic Letters·Hiromichi FujiokaTomohiro Maegawa
Sep 25, 2007·The Journal of Organic Chemistry·Hiromichi FujiokaYasuyuki Kita
Feb 13, 2019·The Journal of Organic Chemistry·Takahiro KawajiriYoshinari Sawama
Aug 27, 2019·Journal of the American Chemical Society·Xirui HuThomas J Maimone
Apr 28, 2006·Journal of the American Chemical Society·Hiromichi FujiokaYasuyuki Kita

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