Literature DB >> 21449594

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

Ming Chen1, William R Roush.   

Abstract

The enantioconvergent hydroboration of racemic allenylstannane (±)-1 with ((d)Ipc)(2)BH converts both enantiomers of (±)-1 into the enantioenriched crotylborane (S)-E-3. Subsequent crotylboration of aldehydes with (S)-E-3 provides (E)-stannyl-homoallylic alcohols 5 in good yields and with excellent enantioselectivity.

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Year:  2011        PMID： 21449594      PMCID： PMC3086366          DOI： 10.1021/ja2010187

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


  16 in total

1.  Synthesis of chiral, enantiopure zirconocene imido complexes: highly selective kinetic resolution and stereoinversion of allenes, and evidence for a stepwise cycloaddition/retrocycloaddition reaction mechanism.

Authors:  Z K Sweeney; J L Salsman; R A Andersen; R G Bergman
Journal:  Angew Chem Int Ed Engl       Date:  2000-07-03       Impact factor: 15.336

2.  Efficiency in nonenzymatic kinetic resolution.

Authors:  Edwin Vedejs; Mara Jure
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-27       Impact factor: 15.336

3.  Asymmetric synthesis of alpha-substituted allyl boranes and their application in the synthesis of iso-agatharesinol.

Authors:  Guang Yu Fang; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes.

Authors:  Zhibin Zhang; Christopher F Bender; Ross A Widenhoefer
Journal:  J Am Chem Soc       Date:  2007-10-30       Impact factor: 15.419

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.  Direct enantio-convergent transformation of racemic substrates without racemization or symmetrization.

Authors:  Hajime Ito; Shun Kunii; Masaya Sawamura
Journal:  Nat Chem       Date:  2010-08-29       Impact factor: 24.427

7.  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

8.  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

9.  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

10.  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
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  16 in total

1.  Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes.

Authors:  Patrick T Bohan; F Dean Toste
Journal:  J Am Chem Soc       Date:  2017-08-03       Impact factor: 15.419

2.  Total synthesis of (-)-tirandamycin C.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2011-12-07       Impact factor: 6.005

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.  Enantioselective synthesis of (+)-crocacin C. An example of a highly challenging mismatched double asymmetric δ-stannylcrotylboration reaction.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2012-03-12       Impact factor: 6.005

5.  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

6.  Crotylboron-based synthesis of the polypropionate units of chaxamycins A/D, salinisporamycin, and rifamycin S.

Authors:  Ming Chen; William R Roush
Journal:  J Org Chem       Date:  2012-06-15       Impact factor: 4.354

7.  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

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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