Literature DB >> 17036145

Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1,3-diketones.

Duanpen Lertpibulpanya1, Stephen P Marsden.   

Abstract

Readily prepared 2-alkyl-2-azidopropylcycloalkyl-1,3-diones undergo intramolecular Schmidt rearrangement with a range of hard Lewis acids, leading to indolizidinediones and pyrroloazepinediones. Chiral aluminium-based Lewis acids could also be used to mediate this symmetry-breaking transformation, but no significant asymmetric induction was observed.

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Year:  2006        PMID： 17036145     DOI： 10.1039/b608801e

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  4 in total

1.  Total Synthesis and Characterization of 7-Hypoquinuclidonium Tetrafluoroborate and 7-Hypoquinuclidone BF3 Complex.

Authors:  Marc Liniger; David G VanderVelde; Michael K Takase; Mona Shahgholi; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-01-12       Impact factor: 15.419

2.  Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction.

Authors:  Hashim F Motiwala; Charlie Fehl; Sze-Wan Li; Erin Hirt; Patrick Porubsky; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2013-06-07       Impact factor: 15.419

3.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

4.  Synthesis of densely functionalized enantiopure indolizidines by ring-closing metathesis (RCM) of hydroxylamines from carbohydrate-derived nitrones.

Authors:  Marco Bonanni; Marco Marradi; Francesca Cardona; Stefano Cicchi; Andrea Goti
Journal:  Beilstein J Org Chem       Date:  2007-12-12       Impact factor: 2.883
  4 in total

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