Literature DB >> 22490078

Stereocontrol in a combined allylic azide rearrangement and intramolecular Schmidt reaction.

Ruzhang Liu1, Osvaldo Gutierrez, Dean J Tantillo, Jeffrey Aubé.   

Abstract

Pre-equilibration of an interconverting set of isomeric allylic azides is coupled with an intramolecular Schmidt reaction to afford substituted lactams stereoselectively. The effect of substitution and a preliminary mechanistic study are reported. The synthetic potential of this method is demonstrated in the context of an enantioselective synthesis of an advanced intermediate leading toward pinnaic acid.
© 2012 American Chemical Society

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22490078      PMCID： PMC3340293          DOI： 10.1021/ja300369c

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  22 in total

1.  A tandem Prins/Schmidt reaction approach to marine alkaloids: formal and total syntheses of lepadiformines A and C.

Authors:  Angelica M Meyer; Christopher E Katz; Sze-Wan Li; David Vander Velde; Jeffrey Aubé
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

Review 2.  Synthetic chemistry of halichlorine and the pinnaic acids.

Authors:  Derrick L J Clive; Maolin Yu; Jian Wang; Vince S C Yeh; Shunzhen Kang
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

3.  Asymmetric total synthesis of pinnaic acid.

Authors:  Shu Xu; Hirokazu Arimoto; Daisuke Uemura
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Epoxide-initiated electrophilic cyclization of azides: a novel route for the stereoselective construction of azabicyclic ring systems and total synthesis of (+/-)-indolizidine 167B and 209D.

Authors:  P Ganapati Reddy; Babu Varghese; Sundarababu Baskaran
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

5.  An efficient synthesis of loline alkaloids.

Authors:  Mesut Cakmak; Peter Mayer; Dirk Trauner
Journal:  Nat Chem       Date:  2011-06-19       Impact factor: 24.427

Review 6.  Azide rearrangements in electron-deficient systems.

Authors:  S Lang; J A Murphy
Journal:  Chem Soc Rev       Date:  2005-11-23       Impact factor: 54.564

7.  Synthesis of the transfer-RNA nucleoside queuosine by using a chiral allyl azide intermediate.

Authors:  Florian Klepper; Eva-Maria Jahn; Volker Hickmann; Thomas Carell
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  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

9.  A formal total synthesis of (+/-)-halichlorine and (+/-)-pinnaic acid.

Authors:  Yosuke Matsumura; Sakae Aoyagi; Chihiro Kibayashi
Journal:  Org Lett       Date:  2004-03-18       Impact factor: 6.005

10.  Asymmetric total synthesis of alkaloids 223A and 6-epi-223A.

Authors:  Partha Ghosh; Weston R Judd; Timothy Ribelin; Jeffrey Aubé
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005
View more
  12 in total

Review 1.  Allylic azides: synthesis, reactivity, and the Winstein rearrangement.

Authors:  Angela S Carlson; Joseph J Topczewski
Journal:  Org Biomol Chem       Date:  2019-05-08       Impact factor: 3.876

2.  "It's a (Kinetic) Trap!" - Selectively Differentiating Allylic Azide Isomers.

Authors:  Joseph J Topczewski; Matthew R Porter
Journal:  Synlett       Date:  2018-07       Impact factor: 2.454

3.  Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.

Authors:  Matthew R Porter; Rami M Shaker; Cristian Calcanas; Joseph J Topczewski
Journal:  J Am Chem Soc       Date:  2018-01-10       Impact factor: 15.419

4.  Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution.

Authors:  En-Chih Liu; Joseph J Topczewski
Journal:  J Am Chem Soc       Date:  2019-03-21       Impact factor: 15.419

5.  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

6.  Practical Electrochemical Anodic Oxidation of Polycyclic Lactams for Late Stage Functionalization.

Authors:  Kevin J Frankowski; Ruzhang Liu; Gregory L Milligan; Kevin D Moeller; Jeffrey Aubé
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-01       Impact factor: 15.336

7.  Evidence for a Sigmatropic and an Ionic Pathway in the Winstein Rearrangement.

Authors:  Amy A Ott; Mary H Packard; Manuel A Ortuño; Alayna Johnson; Victoria P Suding; Christopher J Cramer; Joseph J Topczewski
Journal:  J Org Chem       Date:  2018-06-14       Impact factor: 4.354

8.  On the Winstein rearrangement: equilibrium and mechanism.

Authors:  Amy A Ott; Joseph J Topczewski
Journal:  ARKIVOC       Date:  2019-03-30       Impact factor: 1.140

9.  Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction.

Authors:  Madhuri V Shinde; Rohini S Ople; Ekta Sangtani; Rajesh Gonnade; D Srinivasa Reddy
Journal:  Beilstein J Org Chem       Date:  2015-06-23       Impact factor: 2.883

10.  A concomitant allylic azide rearrangement/intramolecular azide-alkyne cycloaddition sequence.

Authors:  Rakesh H Vekariya; Ruzhang Liu; Jeffrey Aubé
Journal:  Org Lett       Date:  2014-03-17       Impact factor: 6.005
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.