Literature DB >> 21786757

Asymmetric aza-[3+3] annulation in the synthesis of indolizidines: an unexpected reversal of regiochemistry.

Grant S Buchanan1, Huifang Dai, Richard P Hsung, Aleksey I Gerasyuto, Casi M Scheinebeck.   

Abstract

An enantioselective and diastereoselective aza-[3+3] annulation of pyrrolidine-based exo-cyclic vinylogous amides and urethanes with chiral vinyl iminium salts is described. This asymmetric annulation manifold is possible because of an unexpected regiochemical reversal whereby head-to-tail annulations dominated over the predicted head-to-head. It should find prevalent synthetic applications in the enantioselective synthesis of indolizidines.
© 2011 American Chemical Society

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Year:  2011        PMID： 21786757      PMCID： PMC3155627          DOI： 10.1021/ol2017438

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


  45 in total

Review 1.  Indolizidine and quinolizidine alkaloids.

Authors:  J P Michael
Journal:  Nat Prod Rep       Date:  2000-12       Impact factor: 13.423

2.  Significant acceleration of 6 pi-azaelectrocyclization resulting from a remarkable substituent effect and formal synthesis of the ocular age pigment A2-E by a new method for substituted pyridine synthesis.

Authors:  K Tanaka; H Mori; M Yamamoto; S Katsumura
Journal:  J Org Chem       Date:  2001-05-04       Impact factor: 4.354

3.  New mechanistic studies on the proline-catalyzed aldol reaction.

Authors:  Benjamin List; Linh Hoang; Harry J Martin
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-08       Impact factor: 11.205

4.  Direct proline-catalyzed asymmetric alpha-aminoxylation of ketones.

Authors:  Yujiro Hayashi; Junichiro Yamaguchi; Tatsunobu Sumiya; Mitsuru Shoji
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-20       Impact factor: 15.336

5.  Routes to N,N'-unsymmetrically substituted 1,3-diketimines.

Authors:  Kyung-Ho Park; Will J Marshall
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

Review 6.  Asymmetric enamine catalysis.

Authors:  Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

7.  Highly stereoselective formal

Authors: 
Journal:  Org Lett       Date:  2000-04-20       Impact factor: 6.005

8.  Total syntheses of enantiomerically enriched R-(+)- and S-(-)-deplancheine.

Authors:  Nadiya Sydorenko; Craig A Zificsak; Aleksey I Gerasyuto; Richard P Hsung
Journal:  Org Biomol Chem       Date:  2005-04-25       Impact factor: 3.876

9.  A General Approach to the Quinolizidine Alkaloids via an Intramolecular Aza-[3 + 3] Annulation. Synthesis of (±)-2-Deoxy-Lasubine II.

Authors:  Yu Zhang; Aleksey I Gerasyuto; Quincy A Long; Richard P Hsung
Journal:  Synlett       Date:  2008-01-01       Impact factor: 2.454

10.  Direct enantioselective Michael addition of aldehydes to vinyl ketones catalyzed by chiral amines.

Authors:  Paolo Melchiorre; Karl Anker Jørgensen
Journal:  J Org Chem       Date:  2003-05-30       Impact factor: 4.354
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  6 in total

1.  Transition State Gauche Effects Control the Torquoselectivities of the Electrocyclizations of Chiral 1-Azatrienes.

Authors:  Ashay Patel; Joseph R Vella; Zhi-Xiong Ma; R P Hsung; K N Houk
Journal:  J Org Chem       Date:  2015-10-16       Impact factor: 4.354

2.  Exploring the Synthetic Potential of γ-Lactam Derivatives Obtained from a Multicomponent Reaction-Applications as Antiproliferative Agents.

Authors:  Adrián López-Francés; Xabier Del Corte; Zuriñe Serna-Burgos; Edorta Martínez de Marigorta; Francisco Palacios; Javier Vicario
Journal:  Molecules       Date:  2022-06-05       Impact factor: 4.927

3.  Synthesis of functionalized indolizidines through Pauson-Khand cycloaddition of 2-allylpyrrolidines.

Authors:  Michael P McCormack; Stephen P Waters
Journal:  J Org Chem       Date:  2013-01-23       Impact factor: 4.354

4.  Diastereoselective synthesis of chiral 1,3-cyclohexadienals.

Authors:  Aitor Urosa; Ignacio E Tobal; Ángela P de la Granja; M Carmen Capitán; R F Moro; Isidro S Marcos; Narciso M Garrido; Francisca Sanz; Emilio Calle; David Díez
Journal:  PLoS One       Date:  2018-02-13       Impact factor: 3.240

5.  Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes.

Authors:  Krzysztof Dzieszkowski; Izabela Barańska; Zbigniew Rafiński
Journal:  J Org Chem       Date:  2020-04-29       Impact factor: 4.354

6.  Establishing the concept of aza-[3 + 3] annulations using enones as a key expansion of this unified strategy in alkaloid synthesis.

Authors:  Aleksey I Gerasyuto; Zhi-Xiong Ma; Grant S Buchanan; Richard P Hsung
Journal:  Beilstein J Org Chem       Date:  2013-06-18       Impact factor: 2.883
  6 in total

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