Literature DB >> 19271702

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

Pradip Maity1, Salvatore D Lepore.   

Abstract

A significant improvement in the generality and reactivity of MBH-type reactions is made possible by anion catalysis and a 1,3-Brook rearrangement. In this new reaction, both aliphatic and aromatic aldehydes are rapidly added to silylallenes, leading to gamma-carbinol allenoates at low temperatures. The utility of these reaction products is demonstrated by a fast-tracked synthesis of a [3.2.1] bisoxa bicycle that makes up the framework of many biologically active natural products, including vitisinol D, an antithrombotic agent.

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Year:  2009        PMID: 19271702      PMCID: PMC2674362          DOI: 10.1021/ja810136m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  20 in total

1.  Recent advances in the Baylis-Hillman reaction and applications.

Authors:  Deevi Basavaiah; Anumolu Jaganmohan Rao; Tummanapalli Satyanarayana
Journal:  Chem Rev       Date:  2003-03       Impact factor: 60.622

2.  Phosphine-catalyzed [4 + 2] annulation: synthesis of cyclohexenes.

Authors:  Yang S Tran; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2007-10-03       Impact factor: 15.419

3.  The Baylis-Hillman reaction: a novel source of attraction, opportunities, and challenges in synthetic chemistry.

Authors:  Deevi Basavaiah; Kalapala Venkateswara Rao; Raju Jannapu Reddy
Journal:  Chem Soc Rev       Date:  2007-03-23       Impact factor: 54.564

4.  Michael-Stork addition of cyclopentyl enamine to allenyl ketones and esters.

Authors:  Maximilian A Silvestri; Deborah C Bromfield; Salvatore D Lepore
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

5.  Baylis-Hillman reactions of N-tosyl aldimines and aryl aldehydes with 3-methylpenta-3,4-dien-2-one.

Authors:  Gui-Ling Zhao; Min Shi
Journal:  Org Biomol Chem       Date:  2005-09-09       Impact factor: 3.876

6.  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

7.  Resveratrol derivatives from the roots of Vitis thunbergii.

Authors:  Yu-Ling Huang; Wei-Jern Tsai; Chien-Chang Shen; Chien-Chih Chen
Journal:  J Nat Prod       Date:  2005-02       Impact factor: 4.050

8.  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

9.  Overcoming the limitations of the Morita-Baylis-Hillman reaction: a rapid and general synthesis of alpha-alkenyl-beta'-hydroxy thioesters.

Authors:  Emily Tarsis; Anna Gromova; Daniel Lim; Guoqiang Zhou; Don M Coltart
Journal:  Org Lett       Date:  2008-10-10       Impact factor: 6.005

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

Authors:  Pradip Maity; Salvatore D Lepore
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354

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  8 in total

1.  Organo-manganese η2-auxiliary directed reactions: a diastereoselective approach to 2,3-allenols.

Authors:  Animesh Roy; Bilal A Bhat; Salvatore D Lepore
Journal:  Org Lett       Date:  2015-02-09       Impact factor: 6.005

2.  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

3.  Intramolecular [1 + 4 + 1] cycloaddition: establishment of the method.

Authors:  Douglass F Taber; Pengfei Guo; Na Guo
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

4.  Allenyl esters as quenching agents for ruthenium olefin metathesis catalysts.

Authors:  Animesh Roy; Maximilian A Silvestri; Robert A Hall; Salvatore D Lepore
Journal:  Tetrahedron Lett       Date:  2016-11-30       Impact factor: 2.415

5.  Chiral Allenylcarbonyls - Underexploited Building Blocks for Complex Synthesis.

Authors:  Krishna Yadavalli; Salvatore D Lepore
Journal:  Lett Org Chem       Date:  2022-02-01       Impact factor: 0.797

6.  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

7.  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

Review 8.  Organocatalyzed Synthesis of [3.2.1] Bicyclooctanes.

Authors:  Ignacio E Tobal; Alejandro M Roncero; Narciso M Garrido; Isidro S Marcos; David Díez
Journal:  Molecules       Date:  2018-04-28       Impact factor: 4.411

  8 in total

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