Literature DB >> 16706539

Rh-catalyzed enantioselective hydrogenation of vinyl boronates for the construction of secondary boronic esters.

Wesley J Moran1, James P Morken.   

Abstract

[reaction: see text] Rh-catalyzed hydrogenation of prochiral vinyl boronates occurs in an enantioselective fashion in the presence of the chiral ligand Walphos 1. This transformation provides access to chiral secondary organoboronates that are not available from alkene hydroboration reactions. The chiral reaction products should be useful in organic synthesis, and preliminary experiments suggest that they may participate in one-pot amination and homologation reactions.

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Year:  2006        PMID： 16706539     DOI： 10.1021/ol060735u

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


  12 in total

1.  Suzuki-Miyaura cross-coupling of 3-pyridyl triflates with 1-alkenyl-2-pinacol boronates.

Authors:  James R Vyvyan; Jennifer A Dell Née Meyer; Toby J Ligon; Kelsey K Motanic; Hayley S Wall
Journal:  Synthesis (Stuttg)       Date:  2010-11       Impact factor: 3.157

2.  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

3.  Synthesis of vinyl boronates from aldehydes by a practical boron-Wittig reaction.

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  Org Lett       Date:  2015-03-23       Impact factor: 6.005

4.  Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

Authors:  Hilary A Kerchner; John Montgomery
Journal:  Org Lett       Date:  2016-10-27       Impact factor: 6.005

5.  Alpha-selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: practical syntheses of internal vinyl aluminums, halides, or boronates.

Authors:  Fang Gao; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

6.  Efficient C-B bond formation promoted by N-heterocyclic carbenes: synthesis of tertiary and quaternary B-substituted carbons through metal-free catalytic boron conjugate additions to cyclic and acyclic alpha,beta-unsaturated carbonyls.

Authors:  Kang-sang Lee; Adil R Zhugralin; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-06-03       Impact factor: 15.419

7.  (1-bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis.

Authors:  Eric M Woerly; Jonathan E Miller; Martin D Burke
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

8.  Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters.

Authors:  Yazhou Lou; Jun Wang; Gelin Gong; Fanfu Guan; Jiaxiang Lu; Jialin Wen; Xumu Zhang
Journal:  Chem Sci       Date:  2019-11-25       Impact factor: 9.825

9.  Biferrocene-Based Diphosphine Ligands: Synthesis and Application of Walphos Analogues in Asymmetric Hydrogenations.

Authors:  Afrooz Zirakzadeh; Manuela A Groß; Yaping Wang; Kurt Mereiter; Felix Spindler; Walter Weissensteiner
Journal:  Organometallics       Date:  2013-02-11       Impact factor: 3.876

10.  Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes*.

Authors:  Yang Gao; Sima Yazdani; Aaron Kendrick; Glen P Junor; Taeho Kang; Douglas B Grotjahn; Guy Bertrand; Rodolphe Jazzar; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-29       Impact factor: 16.823
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