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Literature DB >> 15186148

alpha-Aminoallylation of aldehydes with ammonia: stereoselective synthesis of homoallylic primary amines.

Masaharu Sugiura¹, Keiichi Hirano, Shu Kobayashi.

Abstract

Three-component reactions of aldehydes, ammonia, and allylboronates were found to provide homoallylic primary amines in high yields with high chemo- and stereoselectivities. A two-step, one-pot, stereoselective synthesis of an uncommon alpha-amino acid, alloisoleucine, was achieved utilizing this reaction.

Entities: Chemical

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Year: 2004 PMID： 15186148 DOI： 10.1021/ja049689o

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

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Cited

9 in total

1. Delayed catalyst function enables direct enantioselective conversion of nitriles to NH₂-amines.

Authors: Shaochen Zhang; Juan Del Pozo; Filippo Romiti; Yucheng Mu; Sebastian Torker; Amir H Hoveyda
Journal: Science Date: 2019-04-05 Impact factor: 47.728

2. Asymmetric allylboration of acyl imines catalyzed by chiral diols.

Authors: Sha Lou; Philip N Moquist; Scott E Schaus
Journal: J Am Chem Soc Date: 2007-11-17 Impact factor: 15.419

3. Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters.

Authors: Rauful Alam; Colin Diner; Sybrand Jonker; Lars Eriksson; Kálmán J Szabó
Journal: Angew Chem Int Ed Engl Date: 2016-10-13 Impact factor: 15.336

4. In situ generation of N-unsubstituted imines from alkyl azides and their applications for imine transfer via copper catalysis.

Authors: Lu Hu; Yahu A Liu; Xuebin Liao
Journal: Sci Adv Date: 2017-08-09 Impact factor: 14.136

alpha-Aminoallylation of aldehydes with ammonia: stereoselective synthesis of homoallylic primary amines.

1. Delayed catalyst function enables direct enantioselective conversion of nitriles to NH₂-amines.

2. Asymmetric allylboration of acyl imines catalyzed by chiral diols.

3. Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters.

4. In situ generation of N-unsubstituted imines from alkyl azides and their applications for imine transfer via copper catalysis.

5. A 2-aza-Cope reactivity-based platform for ratiometric fluorescence imaging of formaldehyde in living cells.

Review 6. The pinene scaffold: its occurrence, chemistry, synthetic utility, and pharmacological importance.

7. Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis.

8. A reactivity-based [¹⁸F]FDG probe for in vivo formaldehyde imaging using positron emission tomography.

9. Metal-free C-C bond formation via coupling of nitrile imines and boronic acids.