Literature DB >> 25859907

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

Zhi-Xiong Ma1, Ashay Patel2, K N Houk2, Richard P Hsung1.   

Abstract

Highly torquoselective electrocyclizations of chiral 1-azatrienes are described. These 1-azatrienes contain an allylic stereocenter that is substituted with a silyl group and are derived in situ from condensation of γ-silyl-substituted enals with vinylogous amides. The ensuing stereoselective ring closures are part of a tandem sequence that constitutes an aza-[3 + 3] annulation method for constructing 1,2-dihydropyridines. Several mechanisms for the formal 1,7-hydrogen shift of these 1-azatrienes were evaluated computationally.

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Year:  2015        PMID： 25859907      PMCID： PMC4547485          DOI： 10.1021/acs.orglett.5b00727

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


  18 in total

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

2.  [1,5]-H shift of aldehyde hydrogen in dienal compounds to produce ketenes.

Authors:  Taku Sakaguchi; Yudai Okuno; Yohei Tsutsumi; Hiroshi Tsuchikawa; Shigeo Katsumura
Journal:  Org Lett       Date:  2011-07-14       Impact factor: 6.005

3.  Regioselectivities of (4 + 3) cycloadditions between furans and oxazolidinone-substituted oxyallyls.

Authors:  Andrew G Lohse; Elizabeth H Krenske; Jennifer E Antoline; K N Houk; Richard P Hsung
Journal:  Org Lett       Date:  2010-11-04       Impact factor: 6.005

4.  Highly stereoselective formal

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

5.  Stereoselectivities and regioselectivities of (4 + 3) cycloadditions between allenamide-derived chiral oxazolidinone-stabilized oxyallyls and furans: experiment and theory.

Authors:  Jennifer E Antoline; Elizabeth H Krenske; Andrew G Lohse; K N Houk; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2011-08-18       Impact factor: 15.419

6.  A novel and highly stereoselective approach to aza-spirocycles. A short total synthesis of 2-epi-(+/-)-perhydrohistrionicotoxin and an unprecedented decarboxylation of 2-pyrones.

Authors:  Michael J McLaughlin; Richard P Hsung; Kevin P Cole; Juliet M Hahn; Jiashi Wang
Journal:  Org Lett       Date:  2002-06-13       Impact factor: 6.005

7.  Highly stereoselective asymmetric 6pi-azaelectrocyclization utilizing the novel 7-alkyl substituted cis-1-amino-2-indanols: formal synthesis of 20-epiuleine.

Authors:  Katsunori Tanaka; Shigeo Katsumura
Journal:  J Am Chem Soc       Date:  2002-08-21       Impact factor: 15.419

8.  Tetronamides as latent acyclic vinylogous amides in formal aza-[3 + 3] cycloaddition reactions with alpha,beta-unsaturated iminium salts. An unexpected rearrangement and an approach to synthesis of substituted piperidines.

Authors:  Nadiya Sydorenko; Richard P Hsung; Ossama Saleh Darwish; Juliet M Hahn; Jia Liu
Journal:  J Org Chem       Date:  2004-10-01       Impact factor: 4.354

9.  Control of regioselectivity and stereoselectivity in (4 + 3) cycloadditions of chiral oxyallyls with unsymmetrically disubstituted furans.

Authors:  Yunfei Du; Elizabeth H Krenske; Jennifer E Antoline; Andrew G Lohse; K N Houk; Richard P Hsung
Journal:  J Org Chem       Date:  2012-07-31       Impact factor: 4.354

10.  Stereoselective formal [3 + 3] cycloaddition approach to cis-1-azadecalins and synthesis of (-)-4a,8a-diepi-pumiliotoxin C. evidence for the first highly stereoselective 6pi-electron electrocyclic ring closures of 1-azatrienes.

Authors:  Heather M Sklenicka; Richard P Hsung; Michael J McLaughlin; Lin-Li Wei; Aleksey I Gerasyuto; William B Brennessel
Journal:  J Am Chem Soc       Date:  2002-09-04       Impact factor: 15.419
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  3 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.  Synthesis of ent-ketorfanol via a C-H alkenylation/torquoselective 6π electrocyclization cascade.

Authors:  Eric M Phillips; Tehetena Mesganaw; Ashay Patel; Simon Duttwyler; Brandon Q Mercado; Kendall N Houk; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-17       Impact factor: 15.336

3.  Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products Sanggenons C and O.

Authors:  Chao Qi; Yuan Xiong; Vincent Eschenbrenner-Lux; Huan Cong; John A Porco
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419
  3 in total

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