Literature DB >> 12423122

Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA.

Timothy J Donohoe1, Kevin Blades, Peter R Moore, Michael J Waring, Jon J G Winter, Madeleine Helliwell, Nicholas J Newcombe, Geoffrey Stemp.   

Abstract

The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented. Under these conditions, hydrogen bonding control leads to the (contrasteric) formation of the syn isomer in almost every example that was examined. Evidence for the bidentate binding of TMEDA to OsO4 is presented and a plausible mechanism described.

Entities:  

Year:  2002        PMID： 12423122     DOI： 10.1021/jo026161y

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


  8 in total

1.  Construction of cyclopentanol derivatives via three-component coupling of silyl glyoxylates, acetylides, and nitroalkenes.

Authors:  Gregory R Boyce; Shubin Liu; Jeffrey S Johnson
Journal:  Org Lett       Date:  2012-01-11       Impact factor: 6.005

2.  Catalytic enantioselective silylation of acyclic and cyclic triols: application to total syntheses of cleroindicins D, F, and C.

Authors:  Zhen You; Amir H Hoveyda; Marc L Snapper
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Unusual reactivity patterns of 1,3,6,8-tetraazatricyclo-[4.4.1.1(3,8)]-dodecane (TATD) towards some reducing agents: synthesis of TMEDA.

Authors:  Augusto Rivera; Jaime Rios-Motta
Journal:  Molecules       Date:  2007-07-19       Impact factor: 4.411

4.  Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays.

Authors:  Ian Cumpstey; Jens Frigell; Elias Pershagen; Tashfeen Akhtar; Elena Moreno-Clavijo; Inmaculada Robina; Dominic S Alonzi; Terry D Butters
Journal:  Beilstein J Org Chem       Date:  2011-08-16       Impact factor: 2.883

5.  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

6.  The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid.

Authors:  Ishmael B Masesane; Andrei S Batsanov; Judith A K Howard; Raju Mondal; Patrick G Steel
Journal:  Beilstein J Org Chem       Date:  2006-05-04       Impact factor: 2.883

7.  Total synthesis of viridicatumtoxin B and analogues thereof: strategy evolution, structural revision, and biological evaluation.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou; Abdelatif ElMarrouni; Lizanne G Nilewski; Kathryn Beabout; Tim T Wang; Yousif Shamoo
Journal:  J Am Chem Soc       Date:  2014-08-15       Impact factor: 15.419

8.  Total synthesis of palau'amine.

Authors:  Kosuke Namba; Kohei Takeuchi; Yukari Kaihara; Masataka Oda; Akira Nakayama; Atsushi Nakayama; Masahiro Yoshida; Keiji Tanino
Journal:  Nat Commun       Date:  2015-11-04       Impact factor: 14.919
  8 in total

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