Literature DB >> 23738497

Nucleophilic addition to silyl-protected five-membered ring oxocarbenium ions governed by stereoelectronic effects.

Vi Tuong Tran1, K A Woerpel.   

Abstract

A series of fused-bicyclic acetals containing a disiloxane ring was investigated to evaluate the source of selectivity in silyl-protected 2-deoxyribose systems. The disiloxane ring unexpectedly enables the diaxial conformer of the cation to be stabilized by an electronegative atom at C-3. This low energy conformer subsequently undergoes stereoelectronically controlled nucleophilic addition to give substituted tetrahydrofurans with high diastereoselectivity.

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Year:  2013        PMID： 23738497      PMCID： PMC3713616          DOI： 10.1021/jo400945j

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


  24 in total

1.  Using stereoelectronic effects to explain selective reactions of 4-substituted five-membered ring oxocarbenium ions.

Authors:  Deborah M Smith; K A Woerpel
Journal:  Org Lett       Date:  2004-06-10       Impact factor: 6.005

Review 2.  Advances in methods and algorithms in a modern quantum chemistry program package.

Authors:  Yihan Shao; Laszlo Fusti Molnar; Yousung Jung; Jörg Kussmann; Christian Ochsenfeld; Shawn T Brown; Andrew T B Gilbert; Lyudmila V Slipchenko; Sergey V Levchenko; Darragh P O'Neill; Robert A DiStasio; Rohini C Lochan; Tao Wang; Gregory J O Beran; Nicholas A Besley; John M Herbert; Ching Yeh Lin; Troy Van Voorhis; Siu Hung Chien; Alex Sodt; Ryan P Steele; Vitaly A Rassolov; Paul E Maslen; Prakashan P Korambath; Ross D Adamson; Brian Austin; Jon Baker; Edward F C Byrd; Holger Dachsel; Robert J Doerksen; Andreas Dreuw; Barry D Dunietz; Anthony D Dutoi; Thomas R Furlani; Steven R Gwaltney; Andreas Heyden; So Hirata; Chao-Ping Hsu; Gary Kedziora; Rustam Z Khalliulin; Phil Klunzinger; Aaron M Lee; Michael S Lee; Wanzhen Liang; Itay Lotan; Nikhil Nair; Baron Peters; Emil I Proynov; Piotr A Pieniazek; Young Min Rhee; Jim Ritchie; Edina Rosta; C David Sherrill; Andrew C Simmonett; Joseph E Subotnik; H Lee Woodcock; Weimin Zhang; Alexis T Bell; Arup K Chakraborty; Daniel M Chipman; Frerich J Keil; Arieh Warshel; Warren J Hehre; Henry F Schaefer; Jing Kong; Anna I Krylov; Peter M W Gill; Martin Head-Gordon
Journal:  Phys Chem Chem Phys       Date:  2006-06-12       Impact factor: 3.676

3.  Synthesis of docosasaccharide arabinan motif of mycobacterial cell wall.

Authors:  Akihiro Ishiwata; Yukishige Ito
Journal:  J Am Chem Soc       Date:  2011-02-02       Impact factor: 15.419

4.  Disiloxane-protected 2-deoxyribonolactone as an efficient precursor to 1,2-dideoxy-1-beta-aryl-D-ribofuranoses.

Authors:  U Wichai; S A Woski
Journal:  Org Lett       Date:  1999-10-21       Impact factor: 6.005

5.  Synthesis and characterization of oligodeoxynucleotides containing formamidopyrimidine lesions and nonhydrolyzable analogues.

Authors:  Kazuhiro Haraguchi; Michael O Delaney; Carissa J Wiederholt; Aruna Sambandam; Zsolt Hantosi; Marc M Greenberg
Journal:  J Am Chem Soc       Date:  2002-04-03       Impact factor: 15.419

6.  Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1]heptane.

Authors:  Gregory K Friestad; Hye Jin Lee
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

7.  Direct and facile syntheses of heterocyclic vinyl-C-nucleosides for recognition of inverted base pairs by DNA triple helix formation: first report by direct Wittig route.

Authors:  Jeffrey H Rothman
Journal:  J Org Chem       Date:  2007-04-14       Impact factor: 4.354

8.  Stereoselective synthesis of a fragment of mycobacterial arabinan.

Authors:  Akihiro Ishiwata; Hiroko Akao; Yukishige Ito
Journal:  Org Lett       Date:  2006-11-23       Impact factor: 6.005

9.  Access to oxetane-containing psico-nucleosides from 2-methyleneoxetanes: a role for neighboring group participation?

Authors:  Yanke Liang; Nathan Hnatiuk; John M Rowley; Bryan T Whiting; Geoffrey W Coates; Paul R Rablen; Martha Morton; Amy R Howell
Journal:  J Org Chem       Date:  2011-11-15       Impact factor: 4.354

10.  Continuum of mechanisms for nucleophilic substitutions of cyclic acetals.

Authors:  Jennifer R Krumper; Walter A Salamant; K A Woerpel
Journal:  Org Lett       Date:  2008-10-10       Impact factor: 6.005
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  4 in total

Review 1.  The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Authors:  Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal:  Chem Rev       Date:  2018-05-30       Impact factor: 60.622

2.  Acceleration of acetal hydrolysis by remote alkoxy groups: evidence for electrostatic effects on the formation of oxocarbenium ions.

Authors:  Angie Garcia; Douglas A L Otte; Walter A Salamant; Jillian R Sanzone; K A Woerpel
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-22       Impact factor: 15.336

3.  Side Chain Conformation and Its Influence on Glycosylation Selectivity in Hexo- and Higher Carbon Furanosides.

Authors:  Sameera Siyabalapitiya Arachchige; David Crich
Journal:  J Org Chem       Date:  2021-12-14       Impact factor: 4.354

4.  Effect of conformational rigidity on the stereoselectivity of nucleophilic additions to five-membered ring bicyclic oxocarbenium ion intermediates.

Authors:  Olga Lavinda; Vi Tuong Tran; K A Woerpel
Journal:  Org Biomol Chem       Date:  2014-09-28       Impact factor: 3.876
  4 in total

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