Literature DB >> 16277359

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

Maximilian A Silvestri1, Deborah C Bromfield, Salvatore D Lepore.   

Abstract

[Chemical reaction: see text] We report the first examples of a Michael-Stork enamine addition to allenyl esters and ketones. Studies reveal that 2 equivalents of enamine are required for optimal yields. In the case of an allenyl methyl ketone, cyclopentyl enamine addition led to 8-oxobicyclo[3.2.1]octane formation, providing evidence for the in situ formation of an enamine intermediate following the initial Michael-Stork reaction.

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Year:  2005        PMID： 16277359     DOI： 10.1021/jo0512103

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


  4 in total

1.  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

2.  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

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.  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
  4 in total

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