The Journal of Organic Chemistry 2017-05-11

Chemoselective Reduction of Azlactones Using Schwartz’s Reagent

Danielle L. J. Pinheiro, Eloah P. Ávila, Gabriel M. F. Batista, Giovanni W. Amarante

Index: 10.1021/acs.joc.7b00820

Full Text: HTML

Abstract

Highly chemoselective addition of Schwartz’s reagent to widely available azlactones is described. This method allows the preparation of challenged functionalized α-amino aldehydes, in good to high isolated yields at room temperature, after only 2 min reaction. The presence of sensitive functionalities or electronic factors does not compromise the potential of the method. The use of an excess of the reducing reagent gave a very functionalized allylic alcohol derivative in 86% yield.

Latest Articles:

Synthesis and Unique Optical Properties of Selenophenyl BODIPYs and Their Linear Oligomers

2018-04-19

[10.1021/acs.joc.8b00782]

Synthesis of 3,5-Disubstituted BODIPYs Bearing N-Containing Five-Membered Heteroaryl Groups via Nucleophilic C–N Bond Formation

2018-04-17

[10.1021/acs.joc.8b00087]

Steric Hindrance Underestimated: It is a Long, Long Way to Tri-tert-alkylamines

2018-04-17

[10.1021/acs.joc.8b00496]

Stereoselective Sequential [4+2]/[2+2] Cycloadditions Involving 2-Alkenylindolenines: An Approach to Densely Functionalized Benzo[b]indolizidines

2018-04-16

[10.1021/acs.joc.8b00346]

Pd-Induced Double C–H Bond Activation in Annulative Syntheses of Bipyrrole Boomerangs: Mechanistic Insights from NMR Spectroscopy and Computation

2018-04-16

[10.1021/acs.joc.8b00630]

More Articles...