Literature DB >> 21615101

Complete facial selectivity in the Diels-Alder reaction of a 5-amino-5-carboxycyclopentadiene derivative.

Simon Kim1, Marco A Ciufolini.   

Abstract

5-tert-Butoxycarbonylamino-5-carbethoxy-2-tert-butyldimethylsilyloxy-cyclopentadiene undergoes a Diels-Alder reaction exclusively from the face syn to the nitrogen functionality. Complete reversal of facial bias may be achieved, but at the cost of diminished reactivity, through steric shielding of the N-syn face.
© 2011 American Chemical Society

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Year:  2011        PMID: 21615101     DOI: 10.1021/ol201236j

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


  1 in total

1.  Formation of Aminocyclopentadienes from Silyldihydropyridines: Ring Contractions Driven by Anion Stabilization.

Authors:  Morgan M Walker; Shuming Chen; Brandon Q Mercado; K N Houk; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2018-04-26       Impact factor: 15.336

  1 in total

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