Literature DB >> 16119928

Reactions of (trialkylsilyl)vinylketenes with lithium ynolates: a new benzannulation strategy.

Wesley F Austin1, Yongjun Zhang, Rick L Danheiser.   

Abstract

(Trialkylsilyl)vinylketenes react with lithium ynolates to produce highly substituted phenols in a new benzannulation strategy that proceeds via the 6pi electrocyclization of an intermediate 3-(oxido)dienylketene. [reaction: see text]

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Year:  2005        PMID： 16119928      PMCID： PMC2897055          DOI： 10.1021/ol051307b

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


  11 in total

1.  Simultaneous and stereoselective construction of planar and axial centers of chirality.

Authors:  L Fogel; R P Hsung; W D Wulff; R D Sommer; A L Rheingold
Journal:  J Am Chem Soc       Date:  2001-06-13       Impact factor: 15.419

2.  Hetero [4 + 2] cycloadditions of (trialkylsilyl)vinylketenes. Synthesis of alpha,beta-unsaturated delta-valerolactones and -lactams.

Authors:  D M Bennett; I Okamoto; R L Danheiser
Journal:  Org Lett       Date:  1999-08-26       Impact factor: 6.005

3.  Stereoselective synthesis of highly substituted cyclopentenones through [4+1] annulations of trialkylsilyl vinyl ketenes with alpha-benzotriazolyl organolithium compounds.

Authors:  Christopher P Davie; Rick L Danheiser
Journal:  Angew Chem Int Ed Engl       Date:  2005-09-12       Impact factor: 15.336

4.  Total synthesis of (-)-cylindrocyclophanes A and F exploiting the reversible nature of the olefin cross metathesis reaction.

Authors:  A B Smith; C M Adams; S A Kozmin; D V Paone
Journal:  J Am Chem Soc       Date:  2001-06-27       Impact factor: 15.419

5.  Synthesis and reactivity of silyl vinylketenes: a formal interrupted Dötz benzannulation with unexpected silyl migration.

Authors:  W H Moser; L Sun; J C Huffman
Journal:  Org Lett       Date:  2001-10-18       Impact factor: 6.005

6.  Amination of Bis(trimethylsilyl)-1,2-bisketene with secondary amines: formation of aminodihydrofuranones

Authors: 
Journal:  J Org Chem       Date:  2000-09-08       Impact factor: 4.354

7.  Synthesis of 2-indanones via [4 + 1] annulation reactions of (trialkylsilyl)arylketenes.

Authors:  Audra M Dalton; Yongjun Zhang; Christopher P Davie; Rick L Danheiser
Journal:  Org Lett       Date:  2002-07-25       Impact factor: 6.005

8.  Chemoselective cyclizations of divinyl ketones to cyclohexenones mediated by Lewis acid and base.

Authors:  Nabi A Magomedov; Piero L Ruggiero; Yuchen Tang
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

9.  Synthesis of heterocycles via palladium pi-olefin and pi-alkyne chemistry.

Authors:  Gilson Zeni; Richard C Larock
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

10.  Synthesis of highly substituted cyclopentenones via the [4 + 1] cycloaddition of nucleophilic carbenes and vinyl ketenes.

Authors:  James H Rigby; Zhengqiang Wang
Journal:  Org Lett       Date:  2003-02-06       Impact factor: 6.005
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  11 in total

1.  Silver-Promoted Benzannulations of Siloxy Alkynes with Pyridinium and Isoquinolinium Salts.

Authors:  Jaime R Cabrera-Pardo; David I Chai; Sergey A Kozmin
Journal:  Adv Synth Catal       Date:  2013-09-16       Impact factor: 5.837

2.  A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks.

Authors:  Wenhan Zhang; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2016-08-11       Impact factor: 15.419

3.  Silver-catalyzed formal inverse electron-demand Diels-Alder reaction of 1,2-diazines and siloxy alkynes.

Authors:  Yunus E Türkmen; Timothy J Montavon; Sergey A Kozmin; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2012-05-24       Impact factor: 15.419

4.  A New Route to Silyl-substituted Cyclobutenones and Silylketenes.

Authors:  Konstantin Benda; Tanja Knoth; Rick L Danheiser; Ernst Schaumann
Journal:  Tetrahedron Lett       Date:  2011-01-05       Impact factor: 2.415

5.  Pericyclic reaction of a zwitterionic salt of an enedione-diazoester. A novel strategy for the synthesis of highly functionalized resorcinols.

Authors:  Yu Liu; Kanwarpal Bakshi; Peter Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

6.  A benzannulation strategy for the synthesis of phenols and heteroaromatic compounds based on the reaction of (trialkylsilyl)vinylketenes with lithium ynolates.

Authors:  Wesley F Austin; Yongjun Zhang; Rick L Danheiser
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

7.  Halogenated catechols from cycloaddition reactions of η-(2-ethoxyvinylketene)iron(0) complexes with 1-haloalkynes.

Authors:  Jimmy Truong; Vioela Caze; Ravish K Akhani; Gayatribahen K Joshi; Lazaros Kakalis; Nikita Matsunaga; Wayne F K Schnatter
Journal:  Tetrahedron Lett       Date:  2010-02-10       Impact factor: 2.415

8.  [3 + 2]-Cycloadditions of Azomethine Imines and Ynolates.

Authors:  Sarah E Winterton; Joseph M Ready
Journal:  Org Lett       Date:  2016-05-24       Impact factor: 6.005

9.  Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes.

Authors:  An Wu; Hui Qian; Wanxiang Zhao; Jianwei Sun
Journal:  Chem Sci       Date:  2020-07-06       Impact factor: 9.825

10.  Non-precious metals catalyze formal [4 + 2] cycloaddition reactions of 1,2-diazines and siloxyalkynes under ambient conditions.

Authors:  Chintan S Sumaria; Yunus E Türkmen; Viresh H Rawal
Journal:  Org Lett       Date:  2014-06-09       Impact factor: 6.005
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