Aryl, Alkyl bis-Silyl Ethers: Rapid Access to Monoprotected Aryl Alkyl and Biaryl Ethers

Sudha V. Ankala; Gabriel Fenteany

doi:10.1055/s-2003-38744

LETTER

Aryl, Alkyl bis-Silyl Ethers: Rapid Access to Monoprotected Aryl Alkyl and Biaryl Ethers

Sudha V. Ankala, Gabriel Fenteany*
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA
Fax: +1(312)9960431; e-Mail: fenteany@uic.edu;

Abstract

Alle Artikel dieser Rubrik

Abstract

A simple one-pot procedure has been developed for the selective etherification of aryl silyl ethers in aryl, alkyl bis-silyl ethers to generate alkyl tert-butyldimethylsilyl-protected aryl alkyl ethers and biaryl ethers in good to excellent yields.

Key words

protecting groups - phenols - LiOH/DMF - ethers - selective etherification

Volltext

Referenzen

References

<A NAME="RS01303ST-1A">1a</A> Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: John Wiley and Sons; New York: 1998.

<A NAME="RS01303ST-1B">1b</A> Kocienski PJ. Protecting Groups Georg Thieme Verlag; Stuttgart: 1994.

<A NAME="RS01303ST-2A">2a</A> Oriyama T. Noda K. Yatabe K. Synlett 1997, 701

<A NAME="RS01303ST-2B">2b</A> Saunders DG. Synthesis 1988, 377

<A NAME="RS01303ST-3A">3a</A> Clark JH. Chem. Rev. 1980, 80: 429

<A NAME="RS01303ST-3B">3b</A> Friestad GK. Branchaud BP. Encyclopedia of Reagents for Organic Synthesis Vol. 2: Paquette LA. John Wiley and Sons; New York: 1995. p.1042

<A NAME="RS01303ST-4A">4a</A> Evans DA. Dinsmore CJ. Ratz AM. Evrard DA. Barrow JC. J. Am. Chem. Soc. 1997, 119: 3417

<A NAME="RS01303ST-4B">4b</A> Boger DL. Kim SH. Mori Y. Weng J.-H. Rogel O. Castle SL. McAtee JJ. J. Am. Chem. Soc. 2001, 123: 1862

<A NAME="RS01303ST-4C">4c</A> Angle SR. Wada T. Tetrahedron Lett. 1997, 38: 7955

<A NAME="RS01303ST-4D">4d</A> Wagner I. Musso H. Angew. Chem., Int. Ed. Engl. 1983, 22: 816

<A NAME="RS01303ST-5">5</A> Xu W. Mohan R. Morissey MM. Tetrahedron Lett. 1997, 42: 7337

<A NAME="RS01303ST-6">6</A> Ankala SV. Fenteany G. Tetrahedron Lett. 2002, 43: 4729

<A NAME="RS01303ST-7">7</A> Mc Henry KT. Ankala SV. Ghosh AK. Fenteany G. ChemBioChem 2002, 11: 1105

<A NAME="RS01303ST-8A">8a</A> Boger DL. Sakya SM. Yohannes D. J. Org. Chem. 1991, 56: 4204

<A NAME="RS01303ST-8B">8b</A> Deshpande VH. Gokhale NJ. Tetrahedron Lett. 1992, 33: 4213

<A NAME="RS01303ST-8C">8c</A> Couladouros EA. Soufli IC. Tetrahedron Lett. 1994, 35: 4409

<A NAME="RS01303ST-8D">8d</A> Rychnovsky SD. Hwang K. Tetrahedron Lett. 1994, 35: 8297

<A NAME="RS01303ST-8E">8e</A> Rychnovsky SD. Hwang K. J. Org. Chem. 1994, 59: 5414

<A NAME="RS01303ST-8F">8f</A> Couladouros EA. Soufli IC. Tetrahedron Lett. 1995, 36: 9369

<A NAME="RS01303ST-8G">8g</A> Couladouros EA. Soufli IC. Moutsos VI. Chadha KR. Chem.-Eur. J. 1998, 4: 33

<A NAME="RS01303ST-9">9</A> Tamai S. Kaneda M. Nakamura SJ. J. Antibiot. 1982, 35: 1130

<A NAME="RS01303ST-10">10</A> Itokawa H. Takeya K. Heterocycles 1993, 35: 1467

<A NAME="RS01303ST-11A">11a</A> Lindley J. Tetrahedron 1984, 40: 1433

<A NAME="RS01303ST-11B">11b</A> Noda H. Niwa M. Yamamura S. Tetrahedron Lett. 1981, 22: 3247

<A NAME="RS01303ST-11C">11c</A> Pearson AJ. Lee K. J. Org. Chem. 1994, 59: 2304

<A NAME="RS01303ST-11D">11d</A> Zhu J. Synlett 1997, 133 ; and the references cited therein

<A NAME="RS01303ST-11E">11e</A> Evans DA. Katz JL. West TR. Tetrahedron Lett. 1998, 39: 2937

<A NAME="RS01303ST-11F">11f</A> Chan DMT. Monaco KL. Wang RP. Winters MP. Tetrahedron Lett. 1998, 39: 2933

<A NAME="RS01303ST-12A">12a</A> Marcoux JF. Doye S. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 10539

<A NAME="RS01303ST-12B">12b</A> Palomo C. Oiarbide M. Lopez R. Gomez-Bengoa E. Chem. Commun. 1998, 2091

<A NAME="RS01303ST-12C">12c</A> Schmittling EA. Sawyer JS. J. Org. Chem. 1993, 58: 3229

<A NAME="RS01303ST-12D">12d</A> Sawyer JS. Schmittling EA. Palkowitz JA. Smith WJ. J. Org. Chem. 1998, 63: 6338

<A NAME="RS01303ST-13">13</A> Couladouros EA. Li T. Moutsos VI. Pitsinos EN. Soufli IC. Bioorg. Med. Chem. Lett. 1999, 9: 2927

Preparation of 8 will be reported elsewhere.

It is noteworthy that the ester groups in both 7a and 7b remained intact after exposure to 3.0 equiv of LiOH/DMF at r.t. and the coupled product 9 could be obtained in excellent yields.