Literature DB >> 19899749

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.

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

Abstract

Density functional theory was used to locate transition states for hydroboration reactions of allenes with 9-borabicyclo[3.3.1]nonane and 10-R-9-borabicyclo[3.3.2]decane, as well as transition states for [1,3]-boratropic shift and aldehyde addition reactions of the derived allylboranes. The origin of kinetic versus thermodynamic control in the allene hydroboration step is described.

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Year:  2009        PMID： 19899749      PMCID： PMC2803353          DOI： 10.1021/ol902364d

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  Asymmetric allyl- and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo[3.3.2]decanes.

Authors:  Carlos H Burgos; Eda Canales; Karl Matos; John A Soderquist
Journal:  J Am Chem Soc       Date:  2005-06-08       Impact factor: 15.419

2.  Stereoselective synthesis of gamma-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2]decane.

Authors:  Jeremy Kister; Amy C DeBaillie; Ricardo Lira; William R Roush
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

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

Authors:  Daniel H Ess; Jeremy Kister; Ming Chen; William R Roush
Journal:  J Org Chem       Date:  2009-11-20       Impact factor: 4.354

4.  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

5.  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
  5 in total
  14 in total

1.  Diastereo- and enantioselective synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via allenylboronate kinetic resolution with ((d)Ipc)2BH and aldehyde allylboration.

Authors:  Jeng-Liang Han; Ming Chen; William R Roush
Journal:  Org Lett       Date:  2012-05-30       Impact factor: 6.005

2.  Enantioconvergent hydroboration of a racemic allene: enantioselective synthesis of (E)-δ-stannyl-anti-homoallylic alcohols via aldehyde crotylboration.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

3.  Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2011-03-16       Impact factor: 6.005

4.  Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin.

Authors:  Jeremy Kister; Philippe Nuhant; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Org Lett       Date:  2011-03-04       Impact factor: 6.005

5.  Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.

Authors:  Philippe Nuhant; Jeremy Kister; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Tetrahedron       Date:  2011-09-02       Impact factor: 2.457

6.  Regioselective allene hydrosilylation catalyzed by N-heterocyclic carbene complexes of nickel and palladium.

Authors:  Zachary D Miller; Wei Li; Tomás R Belderrain; John Montgomery
Journal:  J Am Chem Soc       Date:  2013-10-03       Impact factor: 15.419

7.  Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.

Authors:  Farid W van der Mei; Hiroshi Miyamoto; Daniel L Silverio; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-09       Impact factor: 15.336

8.  Highly stereoselective synthesis of anti,anti-dipropionate stereotriads: a solution to the long-standing problem of challenging mismatched double asymmetric crotylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-02-14       Impact factor: 15.419

9.  Enantioselective synthesis of (E)-δ-silyl-anti-homoallylic alcohols via an enantiodivergent hydroboration-crotylboration reaction of a racemic allenylsilane.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2013-03-27       Impact factor: 6.005

10.  Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin-Hammett controlled double asymmetric crotylboration reactions of (S)-E-αphenyldimethylsilyl( d diisopinocampheyl)-crotylborane.

Authors:  Ming Chen; William R Roush
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457
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