Literature DB >> 20722382

Copper(I)-secondary diamine complex-catalyzed enantioselective conjugate boration of linear β,β-disubstituted enones.

I-Hon Chen1, Motomu Kanai, Masakatsu Shibasaki.   

Abstract

A copper(I)-chiral secondary diamine (L-e) complex catalyzes an enantioselective conjugate boration of β,β-disubstituted enones in high yields and up to 99% ee. Product chiral tertiary organoboronates can be converted to enantiomerically enriched cross-aldol products between ketones without any racemization.

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Year:  2010        PMID： 20722382     DOI： 10.1021/ol101691p

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


  11 in total

1.  Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9-BBN-Derived Ate Complexes.

Authors:  Chunyin Law; Yan Meng; Seung Moh Koo; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-04       Impact factor: 15.336

2.  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

3.  Axial preferences in allylations via the Zimmerman-Traxler transition state.

Authors:  Noga Gilboa; Hao Wang; Kendall N Houk; Ilan Marek
Journal:  Chemistry       Date:  2011-06-03       Impact factor: 5.236

4.  Metal-free catalytic enantioselective C-B bond formation: (pinacolato)boron conjugate additions to α,β-unsaturated ketones, esters, Weinreb amides, and aldehydes promoted by chiral N-heterocyclic carbenes.

Authors:  Hao Wu; Suttipol Radomkit; Jeannette M O'Brien; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-05-04       Impact factor: 15.419

5.  Enantioselective Synthesis of Tertiary β-Boryl Amides by Conjunctive Cross-Coupling of Alkenyl Boronates and Carbamoyl Chlorides.

Authors:  Christopher A Wilhelmsen; Xuntong Zhang; Jesse A Myhill; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-18       Impact factor: 15.336

6.  Mechanism of NHC-Catalyzed Conjugate Additions of Diboron and Borosilane Reagents to α,β-Unsaturated Carbonyl Compounds.

Authors:  Hao Wu; Jeannette M Garcia; Fredrik Haeffner; Suttipol Radomkit; Adil R Zhugralin; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2015-08-11       Impact factor: 15.419

7.  Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration.

Authors:  Veronika M Shoba; Nathan C Thacker; Andrew J Bochat; James M Takacs
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-10       Impact factor: 15.336

Review 8.  Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams.

Authors:  Katherine M Byrd
Journal:  Beilstein J Org Chem       Date:  2015-04-23       Impact factor: 2.883

9.  Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation.

Authors:  Duanyang Kong; Suna Han; Rui Wang; Meina Li; Guofu Zi; Guohua Hou
Journal:  Chem Sci       Date:  2017-04-19       Impact factor: 9.825

10.  Pseudoalteromone B: a novel 15C compound from a marine bacterium Pseudoalteromonas sp. CGH2XX.

Authors:  Yu-Hsin Chen; Jimmy Kuo; Jui-Hsin Su; Tsong-Long Hwang; Yung-Husan Chen; Chia-Hung Lee; Ching-Feng Weng; Ping-Jyun Sung
Journal:  Mar Drugs       Date:  2012-07-20       Impact factor: 6.085
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