Molecules | Free Full-Text | A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis
Generation of 500-Member Library of 10-Alkyl-2-R1,3-R2-4,10-Dihydrobenzo[4,5]imidazo[1,2-α]pyrimidin-4-ones
Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars
Tlais, SF.
Dudley, GB.
Sami F. Tlais, Ronald J. Clark and Gregory B. Dudley * -
Authors' affiliation 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
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.
Tlais SF, Clark RJ, Dudley GB. A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis. Molecules. 2009; 14(12):5216-5222.
Tlais, Sami F.; Clark, Ronald J.; Dudley, Gregory B.	2009. "A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis." Molecules 14, no. 12: 5216-5222.
Molecules | Free Full-Text | A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis
Generation of 500-Member Library of 10-Alkyl-2-R1,3-R2-4,10-Dihydrobenzo[4,5]imidazo[1,2-α]pyrimidin-4-ones
Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars
Tlais, SF.
Dudley, GB.
Sami F. Tlais, Ronald J. Clark and Gregory B. Dudley * -
Authors' affiliation 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 selectiv
ity 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
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.
Tlais SF, Clark RJ, Dudley GB. A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis. Molecules. 2009; 14(12):5216-5222.
Tlais, Sami F.; Clark, Ronald J.; Dudley, Gregory B.	2009. "A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis." Molecules 14, no. 12: 5216-5222.