Literature DB >> 12816469

Asymmetric synthesis of cis-5-tert-butylproline with metal carbenoid NH insertion.

Franklin A Davis1, Bin Yang, Jianghe Deng.   

Abstract

The highly stereoselective intramolecular metal carbenoid insertion reaction of sulfinimine-derived delta-amino alpha-diazoesters is used to prepare cis-5-tert-butylproline. A concerted or nearly concerted metal carbenoid N-H insertion reaction mechanism is proposed.

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Year:  2003        PMID： 12816469     DOI： 10.1021/jo030081s

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

1.  Novel Entry to the Tricyclic Core of Stemofoline and Didehydrostemofoline.

Authors:  Jochen Dietz; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  Toward a total synthesis of the stemofoline alkaloids: Advancement of a 1,3-dipolar cycloaddition strategy.

Authors:  Charles S Shanahan; Nathan O Fuller; Bjoern Ludolph; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2011-08-10       Impact factor: 2.415

3.  Rh-Catalyzed Intermolecular Reactions of α-Alkyl-α-Diazo Carbonyl Compounds with Selectivity over β-Hydride Migration.

Authors:  Andrew DeAngelis; Robert Panish; Joseph M Fox
Journal:  Acc Chem Res       Date:  2015-12-21       Impact factor: 22.384

4.  Rh-catalyzed intermolecular reactions of cyclic α-diazocarbonyl compounds with selectivity over tertiary C-H bond migration.

Authors:  Andrew DeAngelis; Olga Dmitrenko; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2012-06-19       Impact factor: 15.419

5.  Synthesis of polysubstituted pyrroles from sulfinimines (N-sulfinyl imines).

Authors:  Franklin A Davis; Kerisha A Bowen; He Xu; Venkata Velvadapu
Journal:  Tetrahedron       Date:  2008-05-05       Impact factor: 2.457

6.  Methods for the synthesis of polyhydroxylated piperidines by diastereoselective dihydroxylation: exploitation in the two-directional synthesis of aza-C-linked disaccharide derivatives.

Authors:  Andrew Kennedy; Adam Nelson; Alexis Perry
Journal:  Beilstein J Org Chem       Date:  2005-08-26       Impact factor: 2.883

7.  Intermolecular carbene S-H insertion catalysed by engineered myoglobin-based catalysts†.

Authors:  Vikas Tyagi; Rachel B Bonn; Rudi Fasan
Journal:  Chem Sci       Date:  2015-04-01       Impact factor: 9.825

8.  Direct synthesis of imino-C-nucleoside analogues and other biologically active iminosugars.

Authors:  Milan Bergeron-Brlek; Michael Meanwell; Robert Britton
Journal:  Nat Commun       Date:  2015-04-23       Impact factor: 14.919

9.  Enantioselective cis-β-lactam synthesis by intramolecular C-H functionalization from enoldiazoacetamides and derivative donor-acceptor cyclopropenes.

Authors:  Xinfang Xu; Yongming Deng; David N Yim; Peter Y Zavalij; Michael P Doyle
Journal:  Chem Sci       Date:  2015-04-01       Impact factor: 9.825

10.  Rapid detection of tert-butoxycarbonyl-methamphetamine by direct analysis in real time time-of-flight mass spectrometry.

Authors:  Ken-Ichi Sugie; Daisuke Kurakami; Mamoru Akutsu; Koichi Saito
Journal:  Forensic Toxicol       Date:  2018-01-12       Impact factor: 4.096
  10 in total

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