Bifunctionalized allenes. Part XIII. A convenient and efficient method for regioselective synthesis of phosphorylated α-hydroxyallenes with protected and unprotected hydroxy group

Ismail E Ismailov; Ivaylo K Ivanov; Valerij Ch Christov

doi:10.3390/molecules19056309

Bifunctionalized allenes. Part XIII. A convenient and efficient method for regioselective synthesis of phosphorylated α-hydroxyallenes with protected and unprotected hydroxy group

Molecules. 2014 May 16;19(5):6309-29. doi: 10.3390/molecules19056309.

Authors

Ismail E Ismailov¹, Ivaylo K Ivanov¹, Valerij Ch Christov²

Affiliations

¹ Department of Organic Chemistry & Technology, Faculty of Natural Sciences, Konstantin Preslavsky University of Shumen, 115, Universitetska Str., BG-9712 Shumen, Bulgaria. iivanov@shu-bg.net.
² Department of Organic Chemistry & Technology, Faculty of Natural Sciences, Konstantin Preslavsky University of Shumen, 115, Universitetska Str., BG-9712 Shumen, Bulgaria. vchristo@shu-bg.net.

Abstract

The paper describes a convenient and efficient method for regioselective synthesis of phosphorylated α-hydroxyallenes using an atom economical [2,3]-sigmatropic rearrangement of intermediate propargyl phosphites or phosphinites. These can be readily prepared via reaction of protected alkynols with dimethyl chlorophosphite or chlorodiphenyl phosphine respectively in the presence of a base.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkadienes / chemical synthesis*
Alkadienes / chemistry
Cross-Linking Reagents / chemical synthesis*
Cross-Linking Reagents / chemistry
Phosphites / chemistry
Phosphorylation
Stereoisomerism*

Substances

Alkadienes
Cross-Linking Reagents
Phosphites
propadiene