A striking exception to the chelate model for acyclic diastereocontrol: efficient access to a versatile propargyl alcohol for chemical synthesis

Sami F Tlais; Ronald J Clark; Gregory B Dudley

doi:10.3390/molecules14125216

A striking exception to the chelate model for acyclic diastereocontrol: efficient access to a versatile propargyl alcohol for chemical synthesis

Molecules. 2009 Dec 15;14(12):5216-22. doi: 10.3390/molecules14125216.

Authors

Sami F Tlais¹, Ronald J Clark, Gregory B Dudley

Affiliation

¹ Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA. stlais@chem.fsu.edu

Abstract

The four-step, asymmetric synthesis of a chiral propargyl alcohol 1 from (R)-pantolactone is described. A key feature of the synthesis is a diastereoselective acetylide addition to a chiral alpha-alkoxy-aldehyde 7, in which unusual Felkin selectivity is observed, despite the potential for chelation control. Crystalline propargyl alcohol 1 is valuable for complex molecule synthesis, and is easy to prepare in multi-gram quantities and high diastereomeric purity.

Publication types

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

MeSH terms

Alkynes / chemistry*
Chelating Agents / chemistry*
Magnetic Resonance Spectroscopy
Models, Molecular*
Propanols / chemistry*
Spectrometry, Mass, Electrospray Ionization
Stereoisomerism

Substances

Alkynes
Chelating Agents
Propanols
propargyl alcohol