A Mild Deprotection of Trichloroethyl Carbamates Using Indium Metal

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

doi:10.1055/s-2002-31919

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml

Teilen / Bookmarken

Facebook X Linkedin Weibo

PDF herunterladen

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;

Weitere Informationen

Publikationsverlauf

Received 20 March 2002
Publikationsdatum:
07. Februar 2007 (online)

Abstract
Volltext
Referenzen

Lizenzen und Reprints Alle Artikel dieser Rubrik

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Crossref Google Scholar

18

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