A Mild Deprotection of Trichloroethyl Carbamates Using Indium Metal

Tomoko Mineno; Seoung-Ryoung Choi; Mitchell A. Avery

doi:10.1055/s-2002-31919

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 2002(6): 0883-0886
DOI: 10.1055/s-2002-31919

LETTER

A Mild Deprotection of Trichloroethyl Carbamates Using Indium Metal

Tomoko Mineno^a, Seoung-Ryoung Choi^a, Mitchell A. Avery*^a-c
Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, P.O. Box 1848, University, MS 38677-1848, USA
Department of Chemistry, University of Mississippi, P.O. Box 1848, University, MS 38677-1848, USA
National Center for Natural Products Research, University of Mississippi, P.O. Box 1848, University, MS 38677-1848, USA
Fax: +1(662)9155638; e-Mail: mavery@olemiss.edu;

Further Information

Publication History

Received 20 March 2002
Publication Date:
07 February 2007 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

The trichloroethoxycarbonyl moiety was efficiently removed from carbamates to furnish the corresponding amines using indium metal in good to excellent yields.

Key words

indium - deprotection - amines - 2,2,2-trichloroethyl carbamates - chemoselectivity

References

1 Woodward RB. Heusler K. Gosteli J. Naegeli P. Oppolzer W. Ramage R. Ranganathan S. Vorbrüggen H. J. Am. Chem. Soc. 1966, 88: 852

Crossref Search in Google Scholar
2 Windholz TB. Johnston DBR. Tetrahedron Lett. 1967, 27: 2555

Search in Google Scholar
3 Dvorak CA. Schmitz WD. Poon DJ. Pryde DC. Lawson JP. Amos RA. Meyers AI. Angew. Chem. Int. Ed. 2000, 39: 1664

Crossref PubMed Search in Google Scholar
4 Xie C. Runnegar MTC. Snider BB. J. Am. Chem. Soc. 2000, 122: 5017

Crossref Search in Google Scholar
5 Takayama H. Ichikawa T. Kuwajima T. Kitajima M. Seki H. Aimi N. Nonato MG. J. Am. Chem. Soc. 2000, 122: 8635

Crossref Search in Google Scholar
6 Peschko C. Steglich W. Tetrahedron Lett. 2000, 41: 9477

Crossref Search in Google Scholar
7 Just G. Grozinger K. Synthesis 1976, 457

Thieme Connect
8 Hijfte LV. Little RD. J. Org. Chem. 1985, 50: 3940

Search in Google Scholar
9 Semmelhack MF. Heinsohn GE. J. Am. Chem. Soc. 1972, 94: 5139

Crossref Search in Google Scholar
10 Overman LE. Freerks RL. J. Org. Chem. 1981, 46: 2833

Crossref Search in Google Scholar
11 Hancock G. Galpin IJ. Morgan BA. Tetrahedron Lett. 1982, 23: 249

Crossref Search in Google Scholar
12 Dong Q. Anderson CE. Ciufolini MA. Tetrahedron Lett. 1995, 36: 5681

Crossref Search in Google Scholar
13 Eckert H. Ugi I. Angew. Chem. Int. Ed. Engl. 1976, 15: 681

Search in Google Scholar
14 Lakshmikantham MV. Jackson YA. Jones RJ. O’Malley GJ. Ravichandran K. Cava MP. Tetrahedron Lett. 1986, 27: 4687

Crossref Search in Google Scholar
15 Pitts MR. Harrison JR. Moody CJ. J. Chem. Soc., Perkin Trans. 1 2001, 955 ; and references cited therein

Crossref
16 Valluri M. Mineno T. Hindupur RM. Avery MA. Tetrahedron Lett. 2001, 42: 7153

Crossref Search in Google Scholar
17 Windholz TB. Johnston DBR. Tetrahedron Lett. 1967, 2555

Crossref

18

Aldrich Chemical Company. Indium powder, 99.99%. Catalog # 27,795-9.