Literature DB >> 19063594

Selective one-pot synthesis of allenyl and alkynyl esters from beta-ketoesters.

Pradip Maity1, Salvatore D Lepore.   

Abstract

A convenient method is described for the dehydration of beta-ketoesters to generate conjugated and deconjugated alkynyl esters and conjugated allenyl esters. This sequential one-pot method involves the formation of a vinyl triflate monoanion intermediate that leads to the selective formation of alkynes or allenes depending on additives and conditions used. Product outcomes appear to be a function of unique mono- and dianion mechanisms which are described.

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Year:  2009        PMID： 19063594      PMCID： PMC2652892          DOI： 10.1021/jo801563x

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


  14 in total

1.  Some typical advances in the synthetic applications of allenes.

Authors:  Shengming Ma
Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

2.  Strategy for the Preparation of Allenes from alpha,beta-Unsaturated and Saturated Ketones via Enol Phosphates.

Authors:  Kay M. Brummond; Elizabeth A. Dingess; Joseph L. Kent
Journal:  J Org Chem       Date:  1996-09-06       Impact factor: 4.354

3.  Deconjugative conversion of alpha-alkynyl esters to alpha,alpha-disubstituted beta-alkynyl esters.

Authors:  Salvatore D Lepore; Yuanjun He
Journal:  J Org Chem       Date:  2005-05-27       Impact factor: 4.354

4.  Studies on the base-promoted conversion of conjugated alkynyl esters to alpha-substituted alpha-allenyl esters.

Authors:  Salvatore D Lepore; Yuanjun He; Pamela Damisse
Journal:  J Org Chem       Date:  2004-12-24       Impact factor: 4.354

5.  Reaction of allenyl esters with sodium azide: an efficient synthesis of e-vinyl azides and polysubstituted pyrroles.

Authors:  Xian Huang; Ruwei Shen; Tiexin Zhang
Journal:  J Org Chem       Date:  2007-02-16       Impact factor: 4.354

6.  Decarboxylative elimination of enol triflates as a general synthesis of acetylenes.

Authors:  Ian Fleming; Chandrashekar Ramarao
Journal:  Org Biomol Chem       Date:  2004-04-21       Impact factor: 3.876

7.  Lewis acid-mediated reactions of 1-cyclopropyl-2-arylethanone derivatives with allenic ester, ethyl acetoacetate, and methyl acrylate.

Authors:  Min Shi; Xiang-Ying Tang; Yong-Hua Yang
Journal:  J Org Chem       Date:  2008-06-21       Impact factor: 4.354

8.  Thermodynamically favored aldol reaction of propargyl or allenyl esters: regioselective synthesis of carbinol allenoates.

Authors:  Bo Xu; Gerald B Hammond
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Alcohol-assisted phosphine catalysis: one-step syntheses of dihydropyrones from aldehydes and allenoates.

Authors:  Gardner S Creech; Ohyun Kwon
Journal:  Org Lett       Date:  2008-01-04       Impact factor: 6.005

10.  Stereoselective synthesis of acetoacetate-derived enol triflates.

Authors:  David Babinski; Omid Soltani; Doug E Frantz
Journal:  Org Lett       Date:  2008-06-10       Impact factor: 6.005
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  6 in total

1.  Catalytic synthesis of nonracemic azaproline derivatives by cyclization of β-alkynyl hydrazines under kinetic resolution conditions.

Authors:  Pradip Maity; Salvatore D Lepore
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-15       Impact factor: 15.336

2.  Diversification reactions of γ-silyl allenyl esters: selective conversion to all-carbon quaternary centers and γ-allene dicarbinols.

Authors:  Susovan Jana; Animesh Roy; Salvatore D Lepore
Journal:  Chem Commun (Camb)       Date:  2017-05-04       Impact factor: 6.222

3.  Anion-catalyzed addition of gamma-silylallenyl esters to aldehydes: a new entry into [3.2.1] bicyclic natural products.

Authors:  Pradip Maity; Salvatore D Lepore
Journal:  J Am Chem Soc       Date:  2009-04-01       Impact factor: 15.419

4.  Zinc(II) catalyzed conversion of alkynes to vinyl triflates in the presence of silyl triflates.

Authors:  Mohammed H Al-huniti; Salvatore D Lepore
Journal:  Org Lett       Date:  2014-07-25       Impact factor: 6.005

5.  Annulation reactions of allenyl esters: an approach to bicyclic diones and medium-sized rings.

Authors:  Bilal A Bhat; Samantha L Maki; Elijah J St Germain; Pradip Maity; Salvatore D Lepore
Journal:  J Org Chem       Date:  2014-09-16       Impact factor: 4.354

6.  Synthesis of highly functionalized tri- and tetrasubstituted alkenes via Pd-catalyzed 1,2-hydrovinylation of terminal 1,3-dienes.

Authors:  Vaneet Saini; Mark O'Dair; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-01-06       Impact factor: 15.419
  6 in total

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