Literature DB >> 23534391

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

Ming Chen1, William R Roush.   

Abstract

The enantioselective hydroboration of racemic allenylsilane (±)-4 with ((d)Ipc)2BH proceeds via enantiodivergent pathways to give vinylborane 11 and crotylborane intermediate (S)-E-5. Subsequent crotylboration of aldehyde substrates with (S)-E-5 at -78 °C provides (E)-δ-silyl-anti-homoallylic alcohols in 71-89% yield and with 93-96% ee.

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Year:  2013        PMID： 23534391      PMCID： PMC3663895          DOI： 10.1021/ol4004405

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


  24 in total

1.  Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds.

Authors:  Ian Fleming; Asuncion Barbero; David Walter
Journal:  Chem Rev       Date:  1997-10-01       Impact factor: 60.622

2.  Parallel kinetic resolutions of monosubstituted succinic anhydrides catalyzed by a modified cinchona alkaloid.

Authors:  Y Chen; L Deng
Journal:  J Am Chem Soc       Date:  2001-11-14       Impact factor: 15.419

3.  Stereoselective synthesis of a model C(18)-C(35) spiroketal fragment of integramycin.

Authors:  Huikai Sun; Jason R Abbott; William R Roush
Journal:  Org Lett       Date:  2011-04-21       Impact factor: 6.005

4.  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

Review 5.  Silicon-based cross-coupling reactions in the total synthesis of natural products.

Authors:  Scott E Denmark; Jack H-C Liu
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-12       Impact factor: 15.336

6.  Direct synthesis of (+)-erogorgiaene through a kinetic enantiodifferentiating step.

Authors:  Huw M L Davies; Abbas M Walji
Journal:  Angew Chem Int Ed Engl       Date:  2005-03-04       Impact factor: 15.336

7.  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

8.  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

9.  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

10.  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
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  4 in total

1.  α-Boryl Organometallic Reagents in Catalytic Asymmetric Synthesis.

Authors:  Chenlong Zhang; Weipeng Hu; James P Morken
Journal:  ACS Catal       Date:  2021-08-12       Impact factor: 13.700

2.  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

3.  Enantiodivergent Hydroboration Reactions of a Racemic Allenylsilane with Diisopinocampheylborane and Curtin-Hammett Controlled Double Asymmetric Crotylboration Reactions of (S)-E-α-phenyldimethylsilyl( d diisopinocampheyl)-crotylborane.

Authors:  Ming Chen; William R Roush
Journal:  Tetrahedron       Date:  2013-07-01       Impact factor: 2.457

4.  Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419
  4 in total

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