Literature DB >> 19775159

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

Jeremy Kister1, Amy C DeBaillie, Ricardo Lira, William R Roush.   

Abstract

Kinetically controlled hydroboration of allenes 8 and 14a-d with the readily accessible Soderquist borane 7, which is generated in situ from borohydride 6, constitutes a convenient and preparatively useful method for synthesis of (Z)-gamma-(substituted)allylboranes 9 and 15a-d. These allylboranes undergo highly diastereo- (> or = 90: 10) and enantioselective (typically 89-96% e.e.) allylboration reactions with representative aldehydes to give syn-beta-functionalized homoallylic alcohols.

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Year:  2009        PMID： 19775159      PMCID： PMC2767336          DOI： 10.1021/ja905494c

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  9 in total

1.  Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

Authors:  Jennifer M Tinsley; Eric Mertz; Pek Y Chong; Robert-André F Rarig; William R Roush
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

2.  Studies on the synthesis of durhamycin A: stereoselective synthesis of a model aglycone.

Authors:  Rajan Pragani; William R Roush
Journal:  Org Lett       Date:  2008-09-23       Impact factor: 6.005

3.  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

4.  Enantioselective synthesis of 1,5-anti- and 1,5-syn-diols using a highly diastereoselective one-pot double allylboration reaction sequence.

Authors:  Eric M Flamme; William R Roush
Journal:  J Am Chem Soc       Date:  2002-11-20       Impact factor: 15.419

5.  Enantioselective synthesis of 2-methyl-1,2-syn- and 2-methyl-1,2-anti-3-butenediols via allene hydroboration-aldehyde allylboration reaction sequences.

Authors:  Ming Chen; Masaki Handa; William R Roush
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

6.  9-Borabicyclo[3.3.2]decanes and the asymmetric hydroboration of 1,1-disubstituted alkenes.

Authors:  Ana Z Gonzalez; José G Román; Eduvigis Gonzalez; Judith Martinez; Jesus R Medina; Karl Matos; John A Soderquist
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

7.  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

8.  Enantio- and diastereoselective synthesis of syn-beta-hydroxyallylsilanes via a chiral (Z)-gamma-silylallylboronate.

Authors:  Ricardo Lira; William R Roush
Journal:  Org Lett       Date:  2007-09-15       Impact factor: 6.005

9.  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
  9 in total
  19 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.  Direct, Mild, and General n-Bu4NBr-Catalyzed Aldehyde Allylsilylation with Allyl Chlorides.

Authors:  Makeda A Tekle-Smith; Kevin S Williamson; Isaac F Hughes; James L Leighton
Journal:  Org Lett       Date:  2017-11-03       Impact factor: 6.005

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.  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
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