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Fluorous Boc (<sup>F</sup>Boc) carbamates: New amine protecting groups for use in fluorous synthesis

Luo, Z and Williams, J and Read, RW and Curran, DP (2001) Fluorous Boc (<sup>F</sup>Boc) carbamates: New amine protecting groups for use in fluorous synthesis. Journal of Organic Chemistry, 66 (12). 4261 - 4266. ISSN 0022-3263

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Abstract

The first fluorous variants of the Boc (tert-butyloxycarbonyl) group have been prepared and tested for their suitability as nitrogen protecting groups. A group with two fluorous chains and an ethylene spacer, (RfCH 2 CH 2 ) 2 (CH 3 )COC(O)-, was readily attached to a representative amine but was difficult to cleave. In contrast, groups with two fluorous chains and a propylene spacer, (RfCH 2 CH 2 CH 2 ) 2 -(CH 3 ) COC(O)-, or one fluorous chain and an ethylene spacer, (RfCH 2 CH 2 )(CH 3 ) 2 COC(O)-, were readily formed and cleaved. The fluorous alcohol component of the F Boc group can be removed by evaporation and can be recovered and reused. The utility of the new F Boc group (C 8 F 17 CH 2 CH 2 )(CH 3 ) 2 COC(O)- was demonstrated in 16 and 96 compound library synthesis exercises. Separations can be achieved either by manual, parallel fluorous solid-phase extraction, or automated, serial fluorous chromatography. The results provide additional confirmation of the value of "light" fluorous synthesis techniques, and the new fluorous Boc groups expand the applicability of fluorous synthesis techniques to many classes of nitrogen-containing organic compounds.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Luo, Z
Williams, J
Read, RW
Curran, DPcurran@pitt.eduCURRAN
Date: 15 June 2001
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 66
Number: 12
Page Range: 4261 - 4266
DOI or Unique Handle: 10.1021/jo010111w
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Amines--chemistry; Carbamates--chemistry; Chromatography, High Pressure Liquid; Fluorine--chemistry; Mass Spectrometry; Molecular Structure
PubMed ID: 11397162
Date Deposited: 14 Feb 2014 17:04
Last Modified: 23 Dec 2017 14:55
URI: http://d-scholarship.pitt.edu/id/eprint/20559

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