Palladium-catalyzed propargylic substitution with phosphorus nucleophiles: efficient, stereoselective synthesis of allenylphosphonates and related compounds

Marcin Kalek; Tommy Johansson; Martina Jezowska; Jacek Stawinski

doi:10.1021/ol102121j

Palladium-catalyzed propargylic substitution with phosphorus nucleophiles: efficient, stereoselective synthesis of allenylphosphonates and related compounds

Org Lett. 2010 Oct 15;12(20):4702-4. doi: 10.1021/ol102121j.

Authors

Marcin Kalek¹, Tommy Johansson, Martina Jezowska, Jacek Stawinski

Affiliation

¹ Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden.

PMID: 20853904
DOI: 10.1021/ol102121j

Abstract

A new, efficient method is developed, based on a palladium(0)-catalyzed reaction of propargylic derivatives with various phosphorus nucleophiles, to produce allenylphosphonates and their analogues with defined stereochemistry in the allenic and the phosphonate moiety.

Publication types

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

MeSH terms

Alkadienes / chemistry*
Catalysis
Molecular Structure
Palladium / chemistry*
Phosphates / chemical synthesis*
Phosphorus / chemistry*
Stereoisomerism

Substances

Alkadienes
Phosphates
Phosphorus
propadiene
Palladium