Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2004(11): 1741-1743
DOI: 10.1055/s-2004-829148
DOI: 10.1055/s-2004-829148
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
A Mild and Efficient Oxidative Deprotection of THP Ethers with NBS in the Presence of β-Cyclodextrin in Water
Further Information
Received
9 February 2004
Publication Date:
13 July 2004 (online)
Publication History
Publication Date:
13 July 2004 (online)
Abstract
An efficient and user-friendly procedure has been developed for the oxidative deprotection of tetrahydropyranyl (THP) ethers with N-bromosuccinimide (NBS) using β-cyclodextrin (β-CD) in water. A series of tetrahydropyranyl ethers were oxidatively deprotected at room temperature in impressive yields.
Key Words
oxidative deprotection - tetrahydropyranyl ethers - N-bromosuccinimide - β-cyclodextrin - water
- 1
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 2nd ed: Wiley; New York: 1991. - 2
Parish EJ.Kizito SA.Heidepriem RW. Synth. Commun. 1993, 23: 223 - 3
Mohammadpoor-Baltork I.Pouranshirvani S. Synthesis 1997, 756 - 4
Mohammadpoor-Baltork I.Hajipour AR.Aghajari M. Synth. Commun. 2002, 32: 1311 - 5
Mohammadpoor-Baltork I.Nourozi AR. Synthesis 1999, 487 - 6
Hajipour AR.Ruoho AE. Synth. Commun. 2003, 33: 871 - 7
Hajipour AR.Mallakpour SE.Baltork IM.Adibi H. Synth. Commun. 2001, 31: 1625 - 8
Heravi MM.Ajami D.Mojtahedi MM.Ghassemzadeh M. Tetrahedron Lett. 1999, 40: 561 - 9
Heravi MM.Ajami D.Ghassemzadeh M. Synthesis 1999, 393 - 10
Nriagu JO.Nieboer E. Chromium in the Natural and Human Environments Wiley; New York: 1998. -
11a
Cusumano JA. J. Chem. Educ. 1995, 72: 959 -
11b
Varma RS.Dahiya R. Tetrahedron Lett. 1997, 38: 2043 - 12
Hajipour AR.Mallakpour SE.Baltork IM.Malakoutikhah M. Tetrahedron 2002, 58: 143 ; and references cited therein -
13a
Krishnaveni NS.Surendra K.Reddy MA.Nageshwar YVD.Rao KR. J. Org. Chem. 2003, 68: 2018 -
13b
Reddy MA.Surendra K.Bhanumathi N.Rao KR. Tetrahedron 2002, 58: 6003 -
13c
Reddy MA.Bhanumathi N.Rao KR. Tetrahedron Lett. 2002, 43: 3237 -
13d
Reddy LR.Reddy MA.Bhanumathi N.Rao KR. Synlett 2000, 339 -
14a
Baltork IM.Pouranshirvani S. Synthesis 1997, 756 -
14b
Baltork IM.Nourozi AR. Synthesis 1999, 487