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

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-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2003(6): 0825-0828
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;

Further Information

Publication History

Received 13 March 2003
Publication Date:
17 April 2003 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

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

References

1a Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: John Wiley and Sons; New York: 1998.

Google Scholar
1b Kocienski PJ. Protecting Groups Georg Thieme Verlag; Stuttgart: 1994.

Google Scholar
2a Oriyama T. Noda K. Yatabe K. Synlett 1997, 701

Article in Thieme Connect Google Scholar
2b Saunders DG. Synthesis 1988, 377

Article in Thieme Connect Google Scholar
3a Clark JH. Chem. Rev. 1980, 80: 429

Crossref Google Scholar
3b Friestad GK. Branchaud BP. Encyclopedia of Reagents for Organic Synthesis Vol. 2: Paquette LA. John Wiley and Sons; New York: 1995. p.1042

Crossref Google Scholar
4a Evans DA. Dinsmore CJ. Ratz AM. Evrard DA. Barrow JC. J. Am. Chem. Soc. 1997, 119: 3417

Crossref Google Scholar
4b Boger DL. Kim SH. Mori Y. Weng J.-H. Rogel O. Castle SL. McAtee JJ. J. Am. Chem. Soc. 2001, 123: 1862

Crossref Google Scholar
4c Angle SR. Wada T. Tetrahedron Lett. 1997, 38: 7955

Crossref Google Scholar
4d Wagner I. Musso H. Angew. Chem., Int. Ed. Engl. 1983, 22: 816

Crossref Google Scholar
5 Xu W. Mohan R. Morissey MM. Tetrahedron Lett. 1997, 42: 7337

Google Scholar
6 Ankala SV. Fenteany G. Tetrahedron Lett. 2002, 43: 4729

Crossref Google Scholar
7 Mc Henry KT. Ankala SV. Ghosh AK. Fenteany G. ChemBioChem 2002, 11: 1105

Google Scholar
8a Boger DL. Sakya SM. Yohannes D. J. Org. Chem. 1991, 56: 4204

Google Scholar
8b Deshpande VH. Gokhale NJ. Tetrahedron Lett. 1992, 33: 4213

Google Scholar
8c Couladouros EA. Soufli IC. Tetrahedron Lett. 1994, 35: 4409

Google Scholar
8d Rychnovsky SD. Hwang K. Tetrahedron Lett. 1994, 35: 8297

Google Scholar
8e Rychnovsky SD. Hwang K. J. Org. Chem. 1994, 59: 5414

Google Scholar
8f Couladouros EA. Soufli IC. Tetrahedron Lett. 1995, 36: 9369

Google Scholar
8g Couladouros EA. Soufli IC. Moutsos VI. Chadha KR. Chem.-Eur. J. 1998, 4: 33

Google Scholar
9 Tamai S. Kaneda M. Nakamura SJ. J. Antibiot. 1982, 35: 1130

Google Scholar
10 Itokawa H. Takeya K. Heterocycles 1993, 35: 1467

Google Scholar
11a Lindley J. Tetrahedron 1984, 40: 1433

Crossref Google Scholar
11b Noda H. Niwa M. Yamamura S. Tetrahedron Lett. 1981, 22: 3247

Crossref Google Scholar
11c Pearson AJ. Lee K. J. Org. Chem. 1994, 59: 2304

Crossref Google Scholar
11d Zhu J. Synlett 1997, 133 ; and the references cited therein

Crossref Google Scholar
11e Evans DA. Katz JL. West TR. Tetrahedron Lett. 1998, 39: 2937

Crossref Google Scholar
11f Chan DMT. Monaco KL. Wang RP. Winters MP. Tetrahedron Lett. 1998, 39: 2933

Crossref Google Scholar
12a Marcoux JF. Doye S. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 10539

Crossref PubMed Google Scholar
12b Palomo C. Oiarbide M. Lopez R. Gomez-Bengoa E. Chem. Commun. 1998, 2091

Crossref PubMed Google Scholar
12c Schmittling EA. Sawyer JS. J. Org. Chem. 1993, 58: 3229

Crossref PubMed Google Scholar
12d Sawyer JS. Schmittling EA. Palkowitz JA. Smith WJ. J. Org. Chem. 1998, 63: 6338

Crossref PubMed Google Scholar
13 Couladouros EA. Li T. Moutsos VI. Pitsinos EN. Soufli IC. Bioorg. Med. Chem. Lett. 1999, 9: 2927

Crossref Google Scholar

14

Preparation of 8 will be reported elsewhere.

15

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.