Literature DB >> 10804579

Highly stereoselective formal

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Abstract

[formula: see text] Highly stereoselective formal [3 + 3] cycloaddition reactions of chiral vinylogous amides with alpha, beta-unsaturated iminiums are described. A mechanistic model is proposed to rationalize the observed stereoselectivity. The 6 pi-electron electrocyclic ring closure appears to be reversible, and a preferred rotation of the alkenyl group, one of the three 2 pi-components, during the ring closure step provides the thermodynamically favored diastereomer as the major product.

Entities:  

Year:  2000        PMID： 10804579     DOI： 10.1021/ol000049+

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


  9 in total

1.  Highly torquoselective electrocyclizations and competing 1,7-hydrogen shifts of 1-azatrienes with silyl substitution at the allylic carbon.

Authors:  Zhi-Xiong Ma; Ashay Patel; K N Houk; Richard P Hsung
Journal:  Org Lett       Date:  2015-04-10       Impact factor: 6.005

2.  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

3.  Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.

Authors:  Grant S Buchanan; John B Feltenberger; Richard P Hsung
Journal:  Curr Org Synth       Date:  2010-08-01       Impact factor: 1.975

4.  A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation.

Authors:  Gang Li; Lauren J Carlson; Irina K Sagamanova; Brian W Slafer; Richard P Hsung; Claudio Gilardi; Heather M Sklenicka; Nadiya Sydroenko
Journal:  Synthesis (Stuttg)       Date:  2009-09-01       Impact factor: 3.157

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

Authors:  Grant S Buchanan; Huifang Dai; Richard P Hsung; Aleksey I Gerasyuto; Casi M Scheinebeck
Journal:  Org Lett       Date:  2011-07-25       Impact factor: 6.005

6.  Total synthesis of (+)-lepadin F.

Authors:  Gang Li; Richard P Hsung; Brian W Slafer; Irina K Sagamanova
Journal:  Org Lett       Date:  2008-09-27       Impact factor: 6.005

7.  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

8.  The [3 + 3]-cycloaddition alternative for heterocycle syntheses: catalytically generated metalloenolcarbenes as dipolar adducts.

Authors:  Xinfang Xu; Michael P Doyle
Journal:  Acc Chem Res       Date:  2014-03-20       Impact factor: 22.384

9.  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
  9 in total

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