Literature DB >> 29024282

Anion Relay Chemistry: Development of an Effective Diastereoselective [3+2] Annulation Tactic Exploiting an Aldol/Brook Rearrangement/Cyclization Cascade.

Heeoon Han1, Amos B Smith1.   

Abstract

An effective [3+2] annulation tactic for the construction of diverse bicyclic compounds possessing highly functionalized cyclopentane rings has been developed employing soft ketone enolates as the initial nucleophile for anion relay chemistry (ARC). The protocol entails a highly diastereoselective aldol/Brook rearrangement/cyclization cascade.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Brook rearrangement; [3+2] annulation; aldol reaction; anion relay chemistry

Mesh：

Substances：

Year:  2017        PMID： 29024282      PMCID： PMC5836311          DOI： 10.1002/anie.201708017

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  20 in total

1.  Total synthesis of the neotropical poison-frog alkaloid (-)-205B.

Authors:  Amos B Smith; Dae-Shik Kim
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

2.  Type II Anion Relay Chemistry: Conformational Constraints To Achieve Effective [1,5]-Vinyl Brook Rearrangements.

Authors:  Qi Liu; Yu Chen; Xiao Zhang; K N Houk; Yong Liang; Amos B Smith
Journal:  J Am Chem Soc       Date:  2017-06-14       Impact factor: 15.419

3.  Diversity-oriented synthesis leads to an effective class of bifunctional linchpins uniting anion relay chemistry (ARC) with benzyne reactivity.

Authors:  Amos B Smith; Won-Suk Kim
Journal:  Proc Natl Acad Sci U S A       Date:  2011-01-18       Impact factor: 11.205

4.  Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via type II anion relay chemistry.

Authors:  Amos B Smith; Heeoon Han; Won-Suk Kim
Journal:  Org Lett       Date:  2011-06-06       Impact factor: 6.005

5.  Benzyl and phenylthiomethyl silanes: a new class of bifunctional linchpins for type II anion relay chemistry (ARC).

Authors:  Amos B Smith; Rongbiao Tong
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

6.  Diterpenoids from the flowers of Rhododendron molle.

Authors:  Shao-Nong Chen; Hua-Ping Zhang; Li-Quan Wang; Guan-Hu Bao; Guo-Wei Qin
Journal:  J Nat Prod       Date:  2004-11       Impact factor: 4.050

7.  A unified synthetic strategy to the Cryptocarya family of natural products exploiting Anion Relay Chemistry (ARC).

Authors:  Bruno Melillo; Amos B Smith
Journal:  Org Lett       Date:  2013-04-24       Impact factor: 6.005

8.  Gram-scale synthesis of (+)-spongistatin 1: development of an improved, scalable synthesis of the F-ring subunit, fragment union, and final elaboration.

Authors:  Amos B Smith; Takashi Tomioka; Christina A Risatti; Jeffrey B Sperry; Chris Sfouggatakis
Journal:  Org Lett       Date:  2008-08-28       Impact factor: 6.005

9.  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

10.  An Effective Bifunctional Aldehyde Linchpin for Type II Anion Relay Chemistry: Development and Application to the Synthesis of a C16-C29 Fragment of Rhizopodin.

Authors:  Bruno Melillo; Ming Z Chen; Roberto Forestieri; Amos B Smith
Journal:  Org Lett       Date:  2015-12-07       Impact factor: 6.005
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  2 in total

Review 1.  Evolution of Anion Relay Chemistry: Construction of Architecturally Complex Natural Products.

Authors:  Yifan Deng; Amos B Smith
Journal:  Acc Chem Res       Date:  2020-04-09       Impact factor: 22.384

2.  Enantioselective Hydrocarbamoylation of Alkenes.

Authors:  Sheng Feng; Yuyang Dong; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-23       Impact factor: 16.823
  2 in total

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