Literature DB >> 19824624

Quantum-mechanical study of 10-R-9-borabicyclo[3.3.2]decane alkene hydroboration.

Daniel H Ess1, Jeremy Kister, Ming Chen, William R Roush.   

Abstract

Density functional theory and correlated ab initio quantum mechanical methods were used to locate and analyze alkene hydroboration transition structures for 10-R-9-borabicyclo[3.3.2]decane reagents. Transition-state ensembles quantitatively modeled enantioselectivity for hydroboration of cis-, trans-, and gem-disubstituted alkenes in excellent agreement with experiment. The 10-R group and borabicyclo[3.3.2]decane ring conformation effects were analyzed to understand the origin of asymmetric selectivity.

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Year:  2009        PMID： 19824624      PMCID： PMC2803351          DOI： 10.1021/jo901737d

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


  18 in total

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2.  Theoretical thermodynamics for large molecules: walking the thin line between accuracy and computational cost.

Authors:  Tobias Schwabe; Stefan Grimme
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3.  Nonracemic homopropargylic alcohols via asymmetric allenylboration with the robust and versatile 10-TMS-9-borabicyclo[3.3.2]decanes.

Authors:  Chunqiu Lai; John A Soderquist
Journal:  Org Lett       Date:  2005-03-03       Impact factor: 6.005

4.  Theory and modeling of stereoselective organic reactions.

Authors:  K N Houk; M N Paddon-Row; N G Rondan; Y D Wu; F K Brown; D C Spellmeyer; J T Metz; Y Li; R J Loncharich
Journal:  Science       Date:  1986-03-07       Impact factor: 47.728

5.  N-propargylamides via the asymmetric michael addition of B-alkynyl-10-TMS-9- borabicyclo[3.3.2]decanes to N-acylimines.

Authors:  Ana Z Gonzalez; Eda Canales; John A Soderquist
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

6.  B-allenyl- and B-(gamma-trimethylsilylpropargyl)-10-phenyl-9-borabicyclo[3.3.2]decanes: asymmetric synthesis of propargyl and alpha-allenyl 3-degree-carbinols from ketones.

Authors:  Eliud Hernandez; Carlos H Burgos; Eyleen Alicea; John A Soderquist
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

7.  Dynamics and the failure of transition state theory in alkene hydroboration.

Authors:  Yatsandra Oyola; Daniel A Singleton
Journal:  J Am Chem Soc       Date:  2009-03-11       Impact factor: 15.419

8.  Asymmetric allylboration reactions with Soderquist's chiral 10-substituted-9-borabicyclo[3.3.2]decanes: a theoretical study.

Authors:  Ariel M Sarotti; Silvina C Pellegrinet
Journal:  J Org Chem       Date:  2009-05-01       Impact factor: 4.354

9.  Borabicyclo[3.3.2]decanes and the stereoselective asymmetric synthesis of 1,3-diol stereotriads from 1,3-diborylpropenes.

Authors:  Ana Z González; José G Román; Eyleen Alicea; Eda Canales; John A Soderquist
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419

10.  Asymmetric gamma-methoxyallylation with the robust 10-TMS-9-borabicyclo[3.3.2]decanes.

Authors:  Lorell Muñoz-Hernández; John A Soderquist
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005
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  2 in total

1.  Enantioselective synthesis of (E)-delta-stannyl homoallylic alcohols via aldehyde allylboration using alpha-stannylallylboranes generated by allene hydroboration followed by a highly diastereoselective 1,3-boratropic shift.

Authors:  Ming Chen; Daniel H Ess; William R Roush
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

2.  Origin of thermodynamic versus kinetic control of allene hydroboration with 9-borabicyclo[3.3.1]nonane and 10(R)-trimethylsilyl-9-borabicyclo[3.3.2]decane.

Authors:  Daniel H Ess; Jeremy Kister; Ming Chen; William R Roush
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005
  2 in total

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