Mild and direct conversion of esters to morpholine amides using diisobutyl(morpholino)aluminum: application to efficient one-pot synthesis of ketones and aldehydes from esters

Morpholine amide intermediates, which are easily prepared by aminolysis of various esters with diisobutyl(morpholino)aluminum, react with organolithium and reducing agents (DIBALH or LDBMA) without isolation of the aminolysis intermediates to give ketones in 83–95% yields and aldehydes quantitativel...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2014-07, Vol.70 (29), p.4420-4424
Main Authors: Jeon, Ah Ram, Kim, Min Eai, Park, Jae Kyo, Shin, Won Kyu, An, Duk Keun
Format: Article
Language:English
Subjects:
Aldehyde
Aldehydes
Amides
Diisobutyl(morpholino)aluminum
Direct conversion
Ester
Esters
Ketone
Ketones
Morpholine
Morpholine amide
Synthesis (chemistry)
Tetrahedrons
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Morpholine amide intermediates, which are easily prepared by aminolysis of various esters with diisobutyl(morpholino)aluminum, react with organolithium and reducing agents (DIBALH or LDBMA) without isolation of the aminolysis intermediates to give ketones in 83–95% yields and aldehydes quantitatively. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.03.045