Literature DB >> 23390951

A catalytic enantioselective tandem allylation strategy for rapid terpene construction: application to the synthesis of pumilaside aglycon.

Grace E Ferris1, Kai Hong, Ian A Roundtree, James P Morken.   

Abstract

Catalytic enantioselective 1,2-diboration of 1,3-dienes followed by cascade allylborations with dicarbonyls provides rapid entry into carbocyclic reaction products. The stereochemical course of this reaction was studied along with its application in the synthesis of pumilaside aglycon.

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Year:  2013        PMID： 23390951      PMCID： PMC3625973          DOI： 10.1021/ja400506j

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


  23 in total

1.  Element-element additions to unsaturated carbon-carbon bonds catalyzed by transition metal complexes.

Authors:  Irina Beletskaya; Christina Moberg
Journal:  Chem Rev       Date:  2006-06       Impact factor: 60.622

2.  Total synthesis of jimenezin via an intramolecular allylboration.

Authors:  Nina G Bandur; David Brückner; Reinhard W Hoffmann; Ulrich Koert
Journal:  Org Lett       Date:  2006-08-17       Impact factor: 6.005

3.  Modular monodentate oxaphospholane ligands: utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes.

Authors:  Christopher H Schuster; Bo Li; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

4.  Electrostatic effects on the reactions of cyclohexanone oxocarbenium ions.

Authors:  Glen Baghdasarian; K A Woerpel
Journal:  J Org Chem       Date:  2006-09-01       Impact factor: 4.354

5.  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

6.  Spectroscopic and X-ray crystallographic evidence for electrostatic effects in 4-substituted cyclohexanone-derived hydrazones, imines, and corresponding salts.

Authors:  David J Dibble; Joseph W Ziller; K A Woerpel
Journal:  J Org Chem       Date:  2011-09-14       Impact factor: 4.354

7.  Pt-catalyzed enantioselective diboration of terminal alkenes with B2(pin)2.

Authors:  Laura T Kliman; Scott N Mlynarski; James P Morken
Journal:  J Am Chem Soc       Date:  2009-09-23       Impact factor: 15.419

Review 8.  Catalytic enantioselective diboration, disilation and silaboration: new opportunities for asymmetric synthesis.

Authors:  Heather E Burks; James P Morken
Journal:  Chem Commun (Camb)       Date:  2007-08-22       Impact factor: 6.222

9.  Secondary deuterium kinetic isotope effects in irreversible additions of allyl reagents to benzaldehyde.

Authors:  Joseph J Gajewski; Wojciech Bocian; Nancy L Brichford; Johanna L Henderson
Journal:  J Org Chem       Date:  2002-06-14       Impact factor: 4.354

10.  Catalytic asymmetric carbohydroxylation of alkenes by a tandem diboration/Suzuki cross-coupling/oxidation reaction.

Authors:  Steven P Miller; Jeremy B Morgan; Felix J Nepveux; James P Morken
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005
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  10 in total

1.  Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling.

Authors:  Gia L Hoang; Zhao-Di Yang; Sean M Smith; Rhitankar Pal; Judy L Miska; Damaris E Pérez; Libbie S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal:  Org Lett       Date:  2015-02-02       Impact factor: 6.005

2.  Enantiomerically enriched tris(boronates): readily accessible conjunctive reagents for asymmetric synthesis.

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  J Am Chem Soc       Date:  2014-11-11       Impact factor: 15.419

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.  Synthesis of medicinally relevant terpenes: reducing the cost and time of drug discovery.

Authors:  Daniel J Jansen; Ryan A Shenvi
Journal:  Future Med Chem       Date:  2014-06       Impact factor: 3.808

7.  Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.

Authors:  Gia L Hoang; James M Takacs
Journal:  Chem Sci       Date:  2017-05-03       Impact factor: 9.825

8.  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

9.  Modular Synthesis of a Versatile Double-Allylation Reagent for Complex Diol Synthesis.

Authors:  Stanna K Dorn; Annika E Tharp; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-11       Impact factor: 16.823

10.  Transition-Metal-Free Borylation of Allylic and Propargylic Alcohols.

Authors:  Núria Miralles; Rauful Alam; Kálmán J Szabó; Elena Fernández
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-02       Impact factor: 15.336
  10 in total

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