Expanding the scope of methyl xanthate esters - From Barton-McCombie reaction auxiliary to versatile protective group

Summary, in English

The methyl xanthate ester is presented as a versatile protective group for alcohols. Hydroxyl groups can easily be transformed into methyl xanthate esters by several methods and are commonly used as an auxiliary in the Barton-McCombie reaction. We show that these methyl xanthate esters can readily and chemoselectively be cleaved under mild conditions by the action of diethylenetriamine using microwave heating. This method is orthogonal to many common hydroxyl protective groups that can be introduced and cleaved in the presence of methyl xanthate ester.

• Author: Karin Thorsheim; Sophie Manner; Ulf Ellervik
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2017
• Language: English
• Pages: 6329-6333
• Publication/Series: Tetrahedron
• Volume: 73
• Issue: 44
• Links: http://dx.doi.org/10.1016/j.tet.2017.09.022
• Document type: Journal article
• Publisher: Elsevier
• Topic: Organic Chemistry
• Keywords: Alcohol protection; Chemoselective; Deprotection; Diethylenetriamine; Methyl xanthate ester
• Status: Published
• ISBN/ISSN/Other: ISSN: 0040-4020