Literature DB >> 19821580

Rh(I)-catalyzed cyclocarbonylation of allenol esters to prepare acetoxy 4-alkylidenecyclopent-3-en-2-ones.

Kay M Brummond1, Matthew M Davis, Chaofeng Huang.   

Abstract

A Rh(I)-catalyzed cyclocarbonylation reaction of allenol esters has been examined and its synthetic viability established for the conversion of trisubstituted allenes to bicyclo[4.3.0] and -[5.3.0] skeletons possessing an alpha-acetoxy cyclopentadienone. Tetrasubstituted allenol acetates gave elimination products, providing examples of a cyclocarbonylation reaction between an alkyne and a latent cumulene or cumulene equivalent. Cleavage of the acetate affords a free hydroxyl group illustrating the utility of this method for accessing alpha-hydroxy carbonyls from allenol esters.

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Year:  2009        PMID： 19821580      PMCID： PMC3433757          DOI： 10.1021/jo901459t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  19 in total

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Journal:  J Org Chem       Date:  1996-04-19       Impact factor: 4.354

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Authors:  D Enders; A Nühring; J Runsink
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8.  Tandem gold(I)-catalyzed cyclization/electrophilic cyclopropanation of vinyl allenes.

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Journal:  Org Lett       Date:  2007-04-25       Impact factor: 6.005

9.  The scope of catalytic enantioselective tandem carbonyl ylide formation-intramolecular [3 + 2] cycloadditions.

Authors:  David M Hodgson; Agnès H Labande; Françoise Y T M Pierard; María A Expósito Castro
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10.  Synthesis of the thapsigargins.

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Journal:  Proc Natl Acad Sci U S A       Date:  2004-06-28       Impact factor: 11.205
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  3 in total

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Journal:  ACS Comb Sci       Date:  2011-02-18       Impact factor: 3.784

2.  Scope and mechanistic investigations of Pd-catalyzed coupling/cyclizations and cycloisomerizations of allenyl malonates.

Authors:  Logan E Vine; Ryan D Reeves; Eleanor M Landwehr; Israel Fernández; Jennifer M Schomaker
Journal:  ACS Catal       Date:  2021-07-15       Impact factor: 13.700

3.  Reactivity and chemoselectivity of allenes in Rh(I)-catalyzed intermolecular (5 + 2) cycloadditions with vinylcyclopropanes: allene-mediated rhodacycle formation can poison Rh(I)-catalyzed cycloadditions.

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  3 in total

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