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Fluorous mixture synthesis of 4-alkylidene cyclopentenones via a rhodium-catalyzed [2+2+1] cycloaddition of alkynyl allenes

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:
CreatorsEmailPitt UsernameORCID
Manku, S
Curran, DPcurran@pitt.eduCURRAN
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: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/19475

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