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Literature DB >> 23976795

A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines. Observation of an Aza-Meyer-Schuster Rearrangement.

Rui Qi¹, Xiao-Na Wang, Kyle A Dekorver, Yu Tang, Chao-Chao Wang, Qian Li, Hui Li, Ming-Can Lv, Qing Yu, Richard P Hsung.

Abstract

Efforts in developing an expeditious and convenient method for synthesizing γ-amino-ynamides via nucleophilic addition of lithiated ynamides to aryl imines are described. This work also features an aza-variant of a Meyer-Schuster rearrangement of γ-amino-ynamides and the synthetic utility of γ-amino-ynamides in an intramolecular ketenimine-[2 + 2] cycloaddition.

Entities: CellLine Chemical Gene

Keywords: Lithiated ynamides; aryl imine addition; aza-Meyer-Schuster rearrangement; azetene; γ–amino-ynamides

Year: 2013 PMID： 23976795 PMCID： PMC3748967 DOI： 10.1055/s-0033-1338476

Source DB: PubMed Journal: Synthesis (Stuttg) ISSN： 0039-7881 Impact factor: 3.157

55 in total

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6. Preparation and synthetic applications of alkene complexes of group 9 transition metals in [2+2+2] cycloaddition reactions.

Authors: Nico Weding; Marko Hapke
Journal: Chem Soc Rev Date: 2011-05-19 Impact factor: 54.564

A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines. Observation of an Aza-Meyer-Schuster Rearrangement.

Review 1. Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

2. Atropisomerism of alpha,beta-unsaturated amidines: stereoselective synthesis by catalytic cascade reaction and optical resolution.

3. Intramolecular ketene-allene cycloadditions.

4. N-Alkynyl imides (ynimides): synthesis and use as a variant of highly labile ethynamine.

5. Catalyst-controlled torquoselectivity switch in the 4π ring-opening reaction of 2-amino-2-azetines giving β-substituted α,β-unsaturated amidines.

6. Preparation and synthetic applications of alkene complexes of group 9 transition metals in [2+2+2] cycloaddition reactions.

7. Synthesis of aminocyclobutanes through ring expansion of N-vinyl-beta-lactams.

8. Synthesis of functionalized allenamides from ynamides by enolate Claisen rearrangement.

9. Novel one-pot approach to synthesis of indanones through Sb(V)-catalyzed reaction of phenylalkynes with aldehydes.

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2. Ynamides in ring forming transformations.