Manku, S and Curran, DP
(2005)
Fluorous mixture synthesis of 4-alkylidene cyclopentenones via a rhodium-catalyzed [2+2+1] cycloaddition of alkynyl allenes.
Journal of Combinatorial Chemistry, 7 (1).
63 - 68.
ISSN 1520-4766
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Abstract
Fluorous mixture synthesis was used to prepare a library of 4-alkylidene cyclopentenones starting from a mixture of four α-amino acid derivatives tagged with different fluorous benzyl carbamates (FCBz) of varying fluorine content. The amino acids were converted to the corresponding propargyl esters and then subjected to an ester-enolate Claisen rearrangement to give a mixture of allenic amino esters. The allenes were then split four ways and propargylated with different propargyl bromides to give four mixtures of alkynyl allenes. The 4-alkylidene cyclopentenones were formed by a formal [2+2+1] cycloaddition of the alkynyl allenes using catalytic [Rh(CO)2Cl] 2 under CO atmosphere. Demixing by fluorous preparative HPLC, removal of the fluorous benzyl carbamates, and then exposure to HCl/ether gave the hydrochloride salts of 16 compounds as diastereomeric mixtures in 69-99% purity. Thus, after just 26 chemical steps, a library of 16 cyclopentenones was prepared by using fluorous mixture synthesis. By comparison, the same library would have required 112 steps if each compound were made individually by parallel synthesis.
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Details
Item Type: |
Article
|
Status: |
Published |
Creators/Authors: |
|
Date: |
1 January 2005 |
Date Type: |
Publication |
Journal or Publication Title: |
Journal of Combinatorial Chemistry |
Volume: |
7 |
Number: |
1 |
Page Range: |
63 - 68 |
DOI or Unique Handle: |
10.1021/cc049899x |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
1520-4766 |
MeSH Headings: |
Alkadienes--chemistry; Alkaloids--chemistry; Catalysis; Chromatography, High Pressure Liquid; Combinatorial Chemistry Techniques; Cyclopentanes--chemical synthesis; Cyclopentanes--chemistry; Fluorine--chemistry; Magnetic Resonance Spectroscopy; Molecular Structure; Rhodium--chemistry |
PubMed ID: |
15638481 |
Date Deposited: |
31 Jul 2013 17:45 |
Last Modified: |
12 Jun 2021 22:56 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/19475 |
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