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Literature DB >> 22430075

Asymmetric synthesis of α-amino boronate esters via organocatalytic pinacolboryl addition to tosylaldimines.

Cristina Solé¹, Henrik Gulyás, Elena Fernández.

Abstract

Organocatalytic nucleophilic pinacolboryl addition from in situ generated MeO(-)→ B(2)pin(2) to C=N double bond can be performed enantioselectively with the aid of chiral phosphines, which promote enantiofacial differentiation in the course of the C-B bond formation. This journal is © The Royal Society of Chemistry 2012

Entities: Chemical

Year: 2012 PMID： 22430075 DOI： 10.1039/c2cc00020b

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

10 in total

1. 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

2. 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

3. 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

4. Reactivity of highly Lewis acidic diborane(4) towards pyridine and isocyanide: formation of boraalkene-pyridine complex and ortho-functionalized pyridine derivatives.

Authors: Yuhei Katsuma; Hiroki Asakawa; Makoto Yamashita
Journal: Chem Sci Date: 2017-12-11 Impact factor: 9.825

10. Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).

Authors: Tomoya Shiro; Anne Schuhmacher; Moritz K Jackl; Jeffrey W Bode
Journal: Chem Sci Date: 2018-05-16 Impact factor: 9.825

10 in total

Asymmetric synthesis of α-amino boronate esters via organocatalytic pinacolboryl addition to tosylaldimines.

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

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

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

4. Reactivity of highly Lewis acidic diborane(4) towards pyridine and isocyanide: formation of boraalkene-pyridine complex and ortho-functionalized pyridine derivatives.

5. Super electron donors derived from diboron.

6. Enantioselective synthesis of α-aminoboronates by NiH-catalysed asymmetric hydroamidation of alkenyl boronates.

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

8. Transition-Metal-Free Borylation of Allylic and Propargylic Alcohols.

9. Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles.

10. Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).