Literature DB >> 18811178

Asymmetric, organocatalytic, three-step synthesis of gamma-hydroxy-(E)-alpha,beta-unsaturated sulfones and esters.

Kimberly S Petersen1, Gary H Posner.   

Abstract

Efficient and enantiocontrolled synthesis of gamma-hydroxy-alpha,beta-unsaturated sulfones and esters are reported through the reaction of enantioenriched alpha-selenyl aldehydes with EWG-stabilized carbanions and then a one-pot selenide oxidation, in situ epoxide formation, and final in situ epoxide opening.

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Year:  2008        PMID： 18811178      PMCID： PMC2628291          DOI： 10.1021/ol8020513

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Organocatalytic asymmetric alpha-selenenylation of aldehydes.

Authors:  Marcello Tiecco; Armando Carlone; Silvia Sternativo; Francesca Marini; Giuseppe Bartoli; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Ether-directed, stereoselective aza-Claisen rearrangements: synthesis of the piperidine alkaloid, alpha-conhydrine.

Authors:  Andrew G Jamieson; Andrew Sutherland
Journal:  Org Lett       Date:  2007-03-20       Impact factor: 6.005

3.  Enantioselective total synthesis of (+)-neosymbioimine.

Authors:  Georgy N Varseev; Martin E Maier
Journal:  Org Lett       Date:  2007-03-23       Impact factor: 6.005

4.  Synthesis of medium-sized cyclic amines by selective ring cleavage of sulfonylated bicyclic amines.

Authors:  F Iradier; R G Arrayás; J C Carretero
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

5.  Enantioconvergent synthesis by sequential asymmetric Horner-Wadsworth-Emmons and palladium-catalyzed allylic substitution reactions.

Authors:  T M Pedersen; E L Hansen; J Kane; T Rein; P Helquist; P O Norrby; D Tanner
Journal:  J Am Chem Soc       Date:  2001-10-10       Impact factor: 15.419

6.  Direct organocatalytic asymmetric alpha-chlorination of aldehydes.

Authors:  Nis Halland; Alan Braunton; Stephan Bachmann; Mauro Marigo; Karl Anker Jørgensen
Journal:  J Am Chem Soc       Date:  2004-04-21       Impact factor: 15.419

7.  A potential route to neuroprostanes and isoprostanes: preparation of the four enantiomerically pure diastereomers of 13-F4t-neuroP.

Authors:  Douglass F Taber; P Ganapati Reddy; Kyle O Arneson
Journal:  J Org Chem       Date:  2008-03-15       Impact factor: 4.354

8.  Highly stereoselective epoxidation of alpha-methyl-gamma-hydroxy-alpha,beta-unsaturated esters: rationalization and synthetic applications.

Authors:  Irakusne López; Santiago Rodríguez; Javier Izquierdo; Florenci V González
Journal:  J Org Chem       Date:  2007-07-26       Impact factor: 4.354
  8 in total
  1 in total

1.  Asymmetric, organocatalytic, three-step synthesis of alpha-hydroxy-(E)-beta,gamma-unsaturated esters.

Authors:  Lindsey C Hess; Gary H Posner
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005
  1 in total

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