A dianionic Ireland-Claisen rearrangement of chiral, nonracemic α-methyl-β-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential utility of the rearrangement for complex molecule synthesis is also demonstrated.
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http://dx.doi.org/10.1021/ol5008422 | DOI Listing |
Org Lett
July 2017
Kenan, Caudill, Venable, and Murray Laboratories of Chemistry University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States.
The synthesis of the briarane-brianthein A core has been accomplished utilizing an extension of the dianionic Ireland-Claisen rearrangement to establish the C1 quaternary carbon and the adjacent C10 ring juncture stereocenters. Two sequential ring-closing metathesis reactions were exploited to construct the 6-10 trans fused ring system.
View Article and Find Full Text PDFOrg Lett
May 2014
Kenan, Caudill, Murray and Venable Laboratories of Chemistry University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States.
A dianionic Ireland-Claisen rearrangement of chiral, nonracemic α-methyl-β-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential utility of the rearrangement for complex molecule synthesis is also demonstrated.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!