Literature DB >> 16928081

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.

Eliud Hernandez1, Carlos H Burgos, Eyleen Alicea, John A Soderquist.   

Abstract

Simple and efficient Grignard procedures are reported for the syntheses of B-allenyl-10-(phenyl)-9-borabicyclo[3.3.2]decane (1) and its B-(gamma-trimethylsilylpropargyl) counterpart (2) in both enantiomeric forms. Both add selectively to ketones, providing propargyl- and alpha-silylallenyl 3-degree-carbinols, respectively (i.e., 6 (61-93% ee) and 9 (64-98% ee)). The air-stable boron byproduct is efficiently recovered and recycled back to either 1 or 2. The ozonolysis and bromination of 9 provide nonracemic alpha-hydroxy acids and gamma-bromopropynyl carbinols, respectively.

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Year:  2006        PMID： 16928081      PMCID： PMC2597672          DOI： 10.1021/ol061596j

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


  6 in total

1.  Chiral allenylboronic esters as practical reagents for enantioselective carbon-carbon bond formation. Facile synthesis of (-)-ipsenol.

Authors:  N Ikeda; I Arai; H Yamamoto
Journal:  J Am Chem Soc       Date:  1986-02-01       Impact factor: 15.419

2.  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

3.  Metal-promoted allylation, propargylation, or allenylation of azetidine-2,3-diones in aqueous and anhydrous media. Application to the asymmetric synthesis of densely functionalized 3-substituted 3-hydroxy-beta-lactams.

Authors:  B Alcaide; P Almendros; C Aragoncillo; R Rodríguez-Acebes
Journal:  J Org Chem       Date:  2001-07-27       Impact factor: 4.354

4.  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

5.  Nonracemic alpha-allenyl carbinols from asymmetric propargylation with the 10-trimethylsilyl-9-borabicyclo[3.3.2]decanes.

Authors:  Eliud Hernandez; John A Soderquist
Journal:  Org Lett       Date:  2005-11-24       Impact factor: 6.005

6.  B-allyl-10-Ph-9-borabicyclo[3.3.2]decanes: strategically designed for the asymmetric allylboration of ketones.

Authors:  Eda Canales; K Ganeshwar Prasad; John A Soderquist
Journal:  J Am Chem Soc       Date:  2005-08-24       Impact factor: 15.419
  6 in total
  9 in total

1.  Catalytic, Enantioselective Synthesis of Allenyl Boronates.

Authors:  De-Wei Gao; Yiyang Xiao; Mingyu Liu; Zhen Liu; Malkanthi K Karunananda; Jason S Chen; Keary M Engle
Journal:  ACS Catal       Date:  2018-03-21       Impact factor: 13.084

2.  Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols.

Authors:  David S Barnett; Scott E Schaus
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

3.  Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

4.  C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation.

Authors:  Tao Liang; Sang Kook Woo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

5.  Chiral Brønsted acid catalyzed enantioselective synthesis of anti-homopropargyl alcohols via kinetic resolution-aldehyde allenylboration using racemic allenylboronates.

Authors:  Andy S Tsai; Ming Chen; William R Roush
Journal:  Org Lett       Date:  2013-03-13       Impact factor: 6.005

6.  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

7.  Catalytic Enantioselective Carbonyl Propargylation Beyond Preformed Carbanions: Reductive Coupling and Hydrogen Auto-Transfer.

Authors:  Brett R Ambler; Sang Kook Woo; Michael J Krische
Journal:  ChemCatChem       Date:  2018-08-07       Impact factor: 5.686

8.  NHC-Cu-catalyzed addition of propargylboron reagents to phosphinoylimines. Enantioselective synthesis of trimethylsilyl-substituted homoallenylamides and application to the synthesis of S-(-)-cyclooroidin.

Authors:  Nicholas W Mszar; Fredrik Haeffner; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-02-20       Impact factor: 15.419

9.  Diastereo- and enantioselective reactions of bis(pinacolato)diboron, 1,3-enynes, and aldehydes catalyzed by an easily accessible bisphosphine-Cu complex.

Authors:  Fanke Meng; Fredrik Haeffner; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-08-04       Impact factor: 15.419
  9 in total

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