Literature DB >> 17988133

Copper-catalyzed enantioselective substitution of allylic carbonates with diboron: an efficient route to optically active alpha-chiral allylboronates.

Hajime Ito1, Shinichiro Ito, Yusuke Sasaki, Kou Matsuura, Masaya Sawamura.   

Abstract

A method for the synthesis of alpha-chiral allylboronates featuring the Cu(I)-catalyzed enantioselective substitution of readily available allylic carbonates with a diboron is described. Using this method, various alpha-chiral allylboronates, including functionalized allylboronates, were successfully synthesized, with high enantiomeric purity.

Entities:  

Year:  2007        PMID： 17988133     DOI： 10.1021/ja076634o

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


  32 in total

1.  Highly (E)-selective BF(3).Et(2)O-promoted allylboration of chiral nonracemic alpha-substituted allylboronates and analysis of the origin of stereocontrol.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

2.  Accessing Both Retention and Inversion Pathways in Stereospecific, Nickel-Catalyzed Miyaura Borylations of Allylic Pivalates.

Authors:  Qi Zhou; Harathi D Srinivas; Songnan Zhang; Mary P Watson
Journal:  J Am Chem Soc       Date:  2016-09-02       Impact factor: 15.419

3.  Enantioselective synthesis of allylboronates bearing a tertiary or quaternary B-substituted stereogenic carbon by NHC-Cu-catalyzed substitution reactions.

Authors:  Aikomari Guzman-Martinez; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-08-11       Impact factor: 15.419

4.  Enantioselective synthesis of boron-substituted quaternary carbon stereogenic centers through NHC-catalyzed conjugate additions of (pinacolato)boron units to enones.

Authors:  Suttipol Radomkit; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-24       Impact factor: 15.336

5.  Mechanism-based enhancement of scope and enantioselectivity for reactions involving a copper-substituted stereogenic carbon centre.

Authors:  Jaehee Lee; Suttipol Radomkit; Sebastian Torker; Juan Del Pozo; Amir H Hoveyda
Journal:  Nat Chem       Date:  2017-10-02       Impact factor: 24.427

6.  Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents.

Authors:  Emma K Edelstein; Sheila Namirembe; James P Morken
Journal:  J Am Chem Soc       Date:  2017-03-29       Impact factor: 15.419

7.  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

8.  Practical, efficient, and broadly applicable synthesis of readily differentiable vicinal diboronate compounds by catalytic three-component reactions.

Authors:  Suttipol Radomkit; Zhenxing Liu; Anna Closs; Malte S Mikus; Amir H Hoveyda
Journal:  Tetrahedron       Date:  2017-05-20       Impact factor: 2.457

9.  Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.

Authors:  Sota Akiyama; Koji Kubota; Malte S Mikus; Paulo H S Paioti; Filippo Romiti; Qinghe Liu; Yuebiao Zhou; Amir H Hoveyda; Hajime Ito
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-16       Impact factor: 15.336

10.  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
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