Copper diisobutyl-t-butoxyaluminum hydride: A novel reagent for chemoselective reduction of tertiary amides over esters. Issue 24 (13th June 2018)

• Record Type: Journal Article
• Authors: Im, So Hee; Shin, Won Kyu; Jaladi, Ashok Kumar; An, Duk Keun
• Is Part Of: Tetrahedron letters. Volume 59:Issue 24(2018)
• Page Start: 2335
• Page End: 2340
• Publication Date: 2018-06-13
• Subjects: Chemoselective reduction -- Tertiary amide -- Ester -- Aldehyde -- CDBBA; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.04.082
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Designing of chemoselective reagent for amide reduction over ester is challenging. New reducing agent CDBBA was developed. The CDBBA exhibited good selectivity for tertiary amide reduction in the presence of ester. This method provides reduction of both aromatic and aliphatic substrates in excellent yields. Abstract: We demonstrate that copper diisobutyl- t -butoxyaluminum hydride, readily prepared from lithium diisobutyl- t -butoxyaluminum hydride and CuI, effectively and chemoselectively reduces tertiary amides over esters at ambient temperature, affording the corresponding aldehydes in excellent yields.