Literature DB >> 26235566

Formal Asymmetric (4+1) Annulation Reaction between Sulfur Ylides and 1,3-Dienes.

Olivier Rousseau1, Thierry Delaunay1, Geoffroy Dequirez1, Tran Trieu-Van1, Koen Robeyns1, Raphaël Robiette2.   

Abstract

A highly enantioselective synthesis of functionalized cyclopentanoids by a formal asymmetric (4+1) annulation strategy was developed. The methodology consists of a stereoselective cyclopropanation reaction between chiral sulfur ylides and 1,3-dienes followed by a, in situ, stereospecific MgI2 -catalyzed rearrangement of vinylcyclopropanes. This method is distinguished by a remarkable compatibility with functional groups and a high stereocontrol.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  annulation; asymmetric synthesis; cyclopentenes; vinylcyclopropanes; ylides

Year:  2015        PMID： 26235566     DOI： 10.1002/chem.201502579

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  2 in total

1.  Asymmetric Synthesis of 2,3-Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o-Quinone Methides.

Authors:  Nicole Meisinger; Lukas Roiser; Uwe Monkowius; Markus Himmelsbach; Raphaël Robiette; Mario Waser
Journal:  Chemistry       Date:  2017-03-27       Impact factor: 5.236

2.  Mild synthesis of isoxazoline derivatives via an efficient [4 + 1] annulation reaction of transient nitrosoalkenes and sulfur ylides.

Authors:  Ting-Bi Hua; Cheng-Xiong Liu; Wei-Min Hu; Long Wang; Qing-Qing Yang
Journal:  Sci Rep       Date:  2021-01-22       Impact factor: 4.379
  2 in total

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