Literature DB >> 12841784

Platinum-catalyzed tandem diboration/asymmetric allylboration: access to nonracemic functionalized 1,3-diols.

Jeremy B Morgan1, James P Morken.   

Abstract

[reaction: see text] A single-pot tandem catalytic diene diboration/carbonyl allylation reaction is described that uses a commercially available chiral diboron reagent. The chirality of the intermediate diboration adduct is transferred to the product in the carbonyl allylation reaction, thereby providing access to enantioenriched chiral products. Notably, the reaction allows for construction of a quaternary stereocenter and furnishes a synthetically versatile C-B bond in the reaction product.

Entities:  

Mesh:

Substances:

Year:  2003        PMID: 12841784     DOI: 10.1021/ol034936z

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


  17 in total

1.  Catalytic enantioselective diboration of cyclic dienes. A modified ligand with general utility.

Authors:  Kai Hong; James P Morken
Journal:  J Org Chem       Date:  2011-09-20       Impact factor: 4.354

2.  Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.

Authors:  Robert E Kyne; Michael C Ryan; Laura T Kliman; James P Morken
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

3.  Axial preferences in allylations via the Zimmerman-Traxler transition state.

Authors:  Noga Gilboa; Hao Wang; Kendall N Houk; Ilan Marek
Journal:  Chemistry       Date:  2011-06-03       Impact factor: 5.236

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.  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.  Asymmetric synthesis of 2 degrees- and 3 degrees-Carbinols via B-methallyl-10-(TMS and Ph)-9-borabicyclo[3.3.2]decanes.

Authors:  José G Roman; John A Soderquist
Journal:  J Org Chem       Date:  2007-11-14       Impact factor: 4.354

7.  Diastereoselective construction of functionalized homoallylic alcohols by Ni-catalyzed diboron-promoted coupling of dienes and aldehydes.

Authors:  Hee Yeon Cho; James P Morken
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

8.  Diastereo-, Enantio-, and anti-Selective Formation of Secondary Alcohol and Quaternary Carbon Stereocenters by Cu-Catalyzed Additions of B-Substituted Allyl Nucleophiles to Carbonyls.

Authors:  Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal:  Org Lett       Date:  2020-11-18       Impact factor: 6.005

9.  Orthogonal reactivity in boryl-substituted organotrifluoroborates.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  J Am Chem Soc       Date:  2008-11-26       Impact factor: 15.419

10.  Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes.

Authors:  John R Coombs; Fredrik Haeffner; Laura T Kliman; James P Morken
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.