Literature DB >> 29120188

α-Silyl Amides: Effective Bifunctional Lynchpins for Type I Anion Relay Chemistry.

Thomas D Montgomery1, Amos B Smith1.   

Abstract

Lynchpins comprising α-silyl amides have been validated for type I anion relay chemistry (ARC) to permit ready access to γ-ketoamides. Importantly, the ARC protocol can be run at ambient temperature without the need of additional reagents to trigger the [1,4] Brook rearrangement.

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Year:  2017        PMID： 29120188      PMCID： PMC5712993          DOI： 10.1021/acs.orglett.7b03142

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


  12 in total

1.  The Spongistatins: Architecturally Complex Natural Products-Part Two: Synthesis of the C(29-51) Subunit, Fragment Assembly, and Final Elaboration to (+)-Spongistatin 2 Financial support was provided by the National Institutes of Health (National Cancer Institute) through Grant CA-70329, a NIH Postdoctoral Fellowship to C.S.B., a Japan Society for Promotion of Science Fellowship to N.M., and a Royal Society Fulbright Fellowship to V.A.D. We also thank the Daiichi Pharmaceutical Co., Ltd, and the Tanabe Seiyaku Co., Ltd for financial support. Finally we thank Dr George T. Furst, Dr. Patrick J. Carroll, and Dr. Rakesh Kohli of the University of Pennsylvania Spectroscopic Service Center for assistance in securing and interpreting high-field NMR spectra, X-ray crystal structures, and mass spectra, respectively.

Authors:  Amos B. Smith III; Qiyan Lin; Victoria A. Doughty; Linghang Zhuang; Mark D. McBriar; Jeffrey K. Kerns; Christopher S. Brook; Noriaki Murase; Kiyoshi Nakayama
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

2.  The Spongistatins: Architecturally Complex Natural Products-Part One: A Formal Synthesis of (+)-Spongistatin 1 by Construction of an Advanced ABCD Fragment Financial support was provided by the National Institutes of Health (National Cancer Institute) through Grant CA-70329, NIH Postdoctoral Fellowships to A.M.B. and W.H.M., a Japan Society for Promotion of Science Fellowship to N.M., and a Royal Society Fulbright Fellowship to V.A.D. We also thank the Daiichi Pharmaceutical Co., Ltd, and the Tanabe Seiyaku Co., Ltd for financial support. Finally we thank Dr. George T. Furst, Dr. Patrick J. Carroll, Dr. Rakesh Kohli, and Mr John Dykins of the University of Pennsylvania Spectroscopic Service Center for assistance in securing and interpreting high-field NMR spectra, X-ray crystal structures, and mass spectra.

Authors:  Amos B. Smith III; Victoria A. Doughty; Qiyan Lin; Linghang Zhuang; Mark D. McBriar; Armen M. Boldi; William H. Moser; Noriaki Murase; Kiyoshi Nakayama; Masao Sobukawa
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

3.  Highly enantioselective intermolecular Stetter reaction of simple acrylates: synthesis of α-chiral γ-ketoesters.

Authors:  Nathalie E Wurz; Constantin G Daniliuc; Frank Glorius
Journal:  Chemistry       Date:  2012-11-14       Impact factor: 5.236

4.  Asymmetric α-photoalkylation of β-ketocarbonyls by primary amine catalysis: facile access to acyclic all-carbon quaternary stereocenters.

Authors:  Yunbo Zhu; Long Zhang; Sanzhong Luo
Journal:  J Am Chem Soc       Date:  2014-09-19       Impact factor: 15.419

5.  Pd-catalyzed carbonylative conjugate addition of dialkylzinc reagents to unsaturated carbonyls.

Authors:  Daniel W Custar; Hai Le; James P Morken
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

6.  Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride.

Authors:  Zhi-Liang Shen; Kelvin Kau Kiat Goh; Hao-Lun Cheong; Colin Hong An Wong; Yin-Chang Lai; Yong-Sheng Yang; Teck-Peng Loh
Journal:  J Am Chem Soc       Date:  2010-10-21       Impact factor: 15.419

7.  Decarboxylative 1,4-Addition of α-Oxocarboxylic Acids with Michael Acceptors Enabled by Photoredox Catalysis.

Authors:  Guang-Zu Wang; Rui Shang; Wan-Min Cheng; Yao Fu
Journal:  Org Lett       Date:  2015-10-02       Impact factor: 6.005

8.  Direct room-temperature lactonisation of alcohols and ethers onto amides: an "amide strategy" for synthesis.

Authors:  Viviana Valerio; Desislava Petkova; Claire Madelaine; Nuno Maulide
Journal:  Chemistry       Date:  2013-01-10       Impact factor: 5.236

9.  Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy.

Authors:  Huili Liu; Kuan Zheng; Xiang Lu; Xiaoxia Wang; Ran Hong
Journal:  Beilstein J Org Chem       Date:  2013-05-23       Impact factor: 2.883

10.  Total Synthesis of (-)-Mandelalide A Exploiting Anion Relay Chemistry (ARC): Identification of a Type II ARC/CuCN Cross-Coupling Protocol.

Authors:  Minh H Nguyen; Masashi Imanishi; Taichi Kurogi; Amos B Smith
Journal:  J Am Chem Soc       Date:  2016-03-08       Impact factor: 15.419
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