Literature DB >> 20496899

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.

Ming Chen1, Daniel H Ess, William R Roush.   

Abstract

A highly enantioselective synthesis of (E)-delta-stannyl homoallylic alcohols 4 via aldehyde allylboration reactions of the double-chiral allylborane reagent 2a is reported. Allylborane 2a was generated from the hydroboration of commercially available allenylstannane 1 with ((d)Ipc)(2)BH at -40 to -20 degrees C followed by a kinetically controlled and highly diastereoselective 1,3-boratropic shift in intermediate 3a.

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Year:  2010        PMID： 20496899      PMCID： PMC2890212          DOI： 10.1021/ja103041u

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


  35 in total

1.  Strained silacycles in organic synthesis: a new reagent for the enantioselective allylation of aldehydes.

Authors:  James W A Kinnaird; Pui Yee Ng; Katsumi Kubota; Xiaolun Wang; James L Leighton
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

2.  Diastereoselective additions of chiral vinylzinc reagents to alpha-chiral aldehydes.

Authors:  James A Marshall; Patrick Eidam
Journal:  Org Lett       Date:  2004-02-05       Impact factor: 6.005

3.  Simple, stable, and versatile double-allylation reagents for the stereoselective preparation of skeletally diverse compounds.

Authors:  Feng Peng; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2007-02-22       Impact factor: 15.419

4.  Acceleration effect of Lewis acid in allylboration of aldehydes: catalytic, regiospecific, diastereospecific, and enantioselective synthesis of homoallyl alcohols.

Authors:  Tatsuo Ishiyama; Taka-aki Ahiko; Norio Miyaura
Journal:  J Am Chem Soc       Date:  2002-10-23       Impact factor: 15.419

5.  Dramatic rate enhancement with preservation of stereospecificity in the first metal-catalyzed additions of allylboronates.

Authors:  Jason W J Kennedy; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2002-10-02       Impact factor: 15.419

6.  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

7.  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

8.  Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol x SnCl4 complexes. optimization, substrate scope and mechanistic investigations.

Authors:  Vivek Rauniyar; Huimin Zhai; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2008-06-07       Impact factor: 15.419

9.  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

10.  Scandium-catalyzed allylboration of aldehydes as a practical method for highly diastereo- and enantioselective construction of homoallylic alcohols.

Authors:  Hugo Lachance; Xiaosong Lu; Michel Gravel; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2003-08-27       Impact factor: 15.419
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  15 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.  Enantioselective synthesis of (-)-basiliskamide A.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2012-02-28       Impact factor: 6.005

3.  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

4.  Catalytic enantioselective 1,2-diboration of 1,3-dienes: versatile reagents for stereoselective allylation.

Authors:  Laura T Kliman; Scott N Mlynarski; Grace E Ferris; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-01       Impact factor: 15.336

5.  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

6.  Studies on the Synthesis of Reidispongiolide A: Stereoselective Synthesis of the C(22)-C(36) Fragment.

Authors:  Maben Ying; William R Roush
Journal:  Tetrahedron       Date:  2011-12-30       Impact factor: 2.457

7.  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

8.  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

9.  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

10.  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
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