A Mild and Efficient Oxidative Deprotection of THP Ethers with NBS in the Presence of β-Cyclodextrin in Water

M. Narender; M. Somi Reddy; K. Rama Rao

doi:10.1055/s-2004-829148

SHORTPAPER

A Mild and Efficient Oxidative Deprotection of THP Ethers with NBS in the Presence of β-Cyclodextrin in Water

M. Narender, M. Somi Reddy, K. Rama Rao*
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India
e-Mail: drkrrao@yahoo.com;

Abstract

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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

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References

<A NAME="RZ02704SS-1">1</A> Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 2nd ed: Wiley; New York: 1991.

<A NAME="RZ02704SS-2">2</A> Parish EJ. Kizito SA. Heidepriem RW. Synth. Commun. 1993, 23: 223

<A NAME="RZ02704SS-3">3</A> Mohammadpoor-Baltork I. Pouranshirvani S. Synthesis 1997, 756

<A NAME="RZ02704SS-4">4</A> Mohammadpoor-Baltork I. Hajipour AR. Aghajari M. Synth. Commun. 2002, 32: 1311

<A NAME="RZ02704SS-5">5</A> Mohammadpoor-Baltork I. Nourozi AR. Synthesis 1999, 487

<A NAME="RZ02704SS-6">6</A> Hajipour AR. Ruoho AE. Synth. Commun. 2003, 33: 871

<A NAME="RZ02704SS-7">7</A> Hajipour AR. Mallakpour SE. Baltork IM. Adibi H. Synth. Commun. 2001, 31: 1625

<A NAME="RZ02704SS-8">8</A> Heravi MM. Ajami D. Mojtahedi MM. Ghassemzadeh M. Tetrahedron Lett. 1999, 40: 561

<A NAME="RZ02704SS-9">9</A> Heravi MM. Ajami D. Ghassemzadeh M. Synthesis 1999, 393

<A NAME="RZ02704SS-10">10</A> Nriagu JO. Nieboer E. Chromium in the Natural and Human Environments Wiley; New York: 1998.

<A NAME="RZ02704SS-11A">11a</A> Cusumano JA. J. Chem. Educ. 1995, 72: 959

<A NAME="RZ02704SS-11B">11b</A> Varma RS. Dahiya R. Tetrahedron Lett. 1997, 38: 2043

<A NAME="RZ02704SS-12">12</A> Hajipour AR. Mallakpour SE. Baltork IM. Malakoutikhah M. Tetrahedron 2002, 58: 143 ; and references cited therein

<A NAME="RZ02704SS-13A">13a</A> Krishnaveni NS. Surendra K. Reddy MA. Nageshwar YVD. Rao KR. J. Org. Chem. 2003, 68: 2018

<A NAME="RZ02704SS-13B">13b</A> Reddy MA. Surendra K. Bhanumathi N. Rao KR. Tetrahedron 2002, 58: 6003

<A NAME="RZ02704SS-13C">13c</A> Reddy MA. Bhanumathi N. Rao KR. Tetrahedron Lett. 2002, 43: 3237

<A NAME="RZ02704SS-13D">13d</A> Reddy LR. Reddy MA. Bhanumathi N. Rao KR. Synlett 2000, 339

<A NAME="RZ02704SS-14A">14a</A> Baltork IM. Pouranshirvani S. Synthesis 1997, 756

<A NAME="RZ02704SS-14B">14b</A> Baltork IM. Nourozi AR. Synthesis 1999, 487