Literature DB >> 16288542

Concatenated catalytic asymmetric allene diboration/allylation/functionalization.

Angela R Woodward1, Heather E Burks, Louis M Chan, James P Morken.   

Abstract

[reaction: see text] Palladium-catalyzed enantioselective diboration of prochiral allenes generates a reactive chiral allylboron intermediate which is a versatile reagent for the allylation of carbonyls. Experiments that improve the enantioselectivity of this process, examine the substrate scope, and are directed toward functionalization of the allylation intermediate are described.

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Year:  2005        PMID： 16288542     DOI： 10.1021/ol052312i

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


  17 in total

1.  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

2.  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

3.  Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.

Authors:  Philippe Nuhant; Jeremy Kister; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Tetrahedron       Date:  2011-09-02       Impact factor: 2.457

4.  Regioselective allene hydrosilylation catalyzed by N-heterocyclic carbene complexes of nickel and palladium.

Authors:  Zachary D Miller; Wei Li; Tomás R Belderrain; John Montgomery
Journal:  J Am Chem Soc       Date:  2013-10-03       Impact factor: 15.419

5.  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

6.  Enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes.

Authors:  Ernest E Lee; Tomislav Rovis
Journal:  Org Lett       Date:  2008-02-20       Impact factor: 6.005

7.  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

8.  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

9.  Cu-catalyzed chemoselective preparation of 2-(pinacolato)boron-substituted allylcopper complexes and their in situ site-, diastereo-, and enantioselective additions to aldehydes and ketones.

Authors:  Fanke Meng; Hwanjong Jang; Byunghyuck Jung; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-03       Impact factor: 15.336

Review 10.  Polyborylated reagents for modern organic synthesis.

Authors:  Masaki Shimizu; Tamejiro Hiyama
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2008       Impact factor: 3.493
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