Literature DB >> 22646839

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.

Jeng-Liang Han1, Ming Chen, William R Roush.   

Abstract

Enantioselective hydroboration of racemic allenylboronate (±)-1 with 0.48 equiv of ((d)Ipc)(2)BH at -25 °C proceeds with efficient kinetic resolution and provides allylborane (R)-Z-4. When heated to 95 °C, allylborane (R)-Z-4 isomerizes to the thermodynamically more stable allylborane isomer (S)-E-7. Subsequent allylboration of aldehydes with (R)-Z-4 or (S)-E-7 at -78 °C followed by oxidative workup provides 1,2-syn- or 1,2-anti-diols, 2 or 3, respectively, in 87-94% ee.

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Year:  2012        PMID： 22646839      PMCID： PMC3426628          DOI： 10.1021/ol3010968

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


  21 in total

1.  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

2.  Catalytic enantioselective allylation of carbonyl compounds and imines.

Authors:  Miguel Yus; José C González-Gómez; Francisco Foubelo
Journal:  Chem Rev       Date:  2011-09-16       Impact factor: 60.622

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.  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

5.  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

6.  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

7.  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

8.  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

9.  Copper(I)-catalyzed substitution of propargylic carbonates with diboron: selective synthesis of multisubstituted allenylboronates.

Authors:  Hajime Ito; Yusuke Sasaki; Masaya Sawamura
Journal:  J Am Chem Soc       Date:  2008-11-26       Impact factor: 15.419

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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  6 in total

1.  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

2.  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

3.  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

4.  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

5.  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

6.  α-Silicon effect assisted Curtin-Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes.

Authors:  Shang Gao; Ming Chen
Journal:  Chem Sci       Date:  2019-06-28       Impact factor: 9.825
  6 in total

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