Literature DB >> 21932816

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

Kai Hong1, James P Morken.   

Abstract

The enantioselective 1,4-diboration of cyclic dienes with a new taddol-derived phosphonite ligand occurs with excellent enantioselectivity. Oxidation delivers the derived 1,4-diol, whereas homologation can be used to deliver a chiral 1,6-diol.

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Year:  2011        PMID： 21932816      PMCID： PMC3219059          DOI： 10.1021/jo201321k

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  12 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.  Nickel-Catalyzed Cross-Coupling of Dienyl Phosphates with Grignard Reagents in the Synthesis of 2-Substituted 1,3-Dienes.

Authors:  A. Sofia. E. Karlström; Kenichiro Itami; Jan-E. Bäckvall
Journal:  J Org Chem       Date:  1999-03-05       Impact factor: 4.354

3.  Catalytic enantioselective three-component hetero-[4+2] cycloaddition/allylboration approach to alpha-hydroxyalkyl pyrans: scope, limitations, and mechanistic proposal.

Authors:  Xuri Gao; Dennis G Hall; Michael Deligny; Annaick Favre; François Carreaux; Bertrand Carboni
Journal:  Chemistry       Date:  2006-04-03       Impact factor: 5.236

4.  Catalytic asymmetric synthesis of a potent thiomarinol antibiotic.

Authors:  Xuri Gao; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2005-02-16       Impact factor: 15.419

5.  Bulky monodentate phosphoramidites in palladium-catalyzed allylic alkylation reactions: aspects of regioselectivity and enantioselectivity.

Authors:  Maarten D K Boele; Paul C J Kamer; Martin Lutz; Anthony L Spek; Johannes G de Vries; Piet W N M van Leeuwen; Gino P F van Strijdonck
Journal:  Chemistry       Date:  2004-12-03       Impact factor: 5.236

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

Authors:  Jeremy B Morgan; James P Morken
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

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.  Metal-catalyzed reactions of diborons for synthesis of organoboron compounds.

Authors:  Tatsuo Ishiyama; Norio Miyaura
Journal:  Chem Rec       Date:  2004       Impact factor: 6.771

Review 10.  Homologation and alkylation of boronic esters and boranes by 1,2-metallate rearrangement of boronate complexes.

Authors:  Stephen P Thomas; Rosalind M French; Vishal Jheengut; Varinder K Aggarwal
Journal:  Chem Rec       Date:  2009       Impact factor: 6.771
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  6 in total

1.  γ-Selective directed catalytic asymmetric hydroboration of 1,1-disubstituted alkenes.

Authors:  Sean M Smith; Gia L Hoang; Rhitankar Pal; Mohammad O Bani Khaled; Liberty S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal:  Chem Commun (Camb)       Date:  2012-12-28       Impact factor: 6.222

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.  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

4.  Direct, redox-neutral prenylation and geranylation of secondary carbinol C-H bonds: C4-regioselectivity in ruthenium-catalyzed C-C couplings of dienes to α-hydroxy esters.

Authors:  Joyce C Leung; Laina M Geary; Te-Yu Chen; Jason R Zbieg; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-09-17       Impact factor: 15.419

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

Authors:  Grace E Ferris; Kai Hong; Ian A Roundtree; James P Morken
Journal:  J Am Chem Soc       Date:  2013-02-07       Impact factor: 15.419

6.  Catalytic enantioselective one-pot aminoborylation of aldehydes: a strategy for construction of nonracemic α-amino boronates.

Authors:  Kai Hong; James P Morken
Journal:  J Am Chem Soc       Date:  2013-06-13       Impact factor: 15.419
  6 in total

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