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Keywords = acyclic diastereocontrol

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7 pages, 236 KB  
Article
A Striking Exception to the Chelate Model for Acyclic Diastereocontrol: Efficient Access to a Versatile Propargyl Alcohol for Chemical Synthesis
by Sami F. Tlais, Ronald J. Clark and Gregory B. Dudley
Molecules 2009, 14(12), 5216-5222; https://doi.org/10.3390/molecules14125216 - 15 Dec 2009
Cited by 6 | Viewed by 11417
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Asymmetric Synthesis)
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