Next Article in Journal
Generation of 500-Member Library of 10-Alkyl-2-R1,3-R2-4,10-Dihydrobenzo[4,5]imidazo[1,2-α]pyrimidin-4-ones
Next Article in Special Issue
Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars
Previous Article in Journal
Synthesis and Antimicrobial Activity of Some Pyridinium Salts
Previous Article in Special Issue
Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids
Molecules 2009, 14(12), 5216-5222; doi:10.3390/molecules14125216
Article

A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis

,
 and
*
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA
* Author to whom correspondence should be addressed.
Received: 26 October 2009 / Revised: 17 November 2009 / Accepted: 30 November 2009 / Published: 15 December 2009
(This article belongs to the Special Issue Asymmetric Synthesis)
Download PDF [236 KB, uploaded 18 June 2014]

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 α-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.
Keywords: pantolactone; synthesis; Felkin–Anh; acyclic diastereocontrol; chiral building block pantolactone; synthesis; Felkin–Anh; acyclic diastereocontrol; chiral building block
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
MDPI and ACS Style

Tlais, S.F.; Clark, R.J.; Dudley, G.B. A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis. Molecules 2009, 14, 5216-5222.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert