855518-87-5Relevant academic research and scientific papers
Regioselective lewis acid-mediated [1,3] rearrangement of allylvinyl ethers
Nasveschuk, Christopher G.,Rovis, Tomislav
, p. 2173 - 2176 (2005)
(Chemical Equation Presented) Aluminum and copper Lewis acids were implemented to effect a regioselective [1,3] rearrangement of allylvinyl ethers in moderate to good yields. The use of trisubstituted alkenes leads to depressed levels of Claisen products.
Asymmetric synthesis of 1,2-dioxolane-3-acetic acids: Synthesis and configurational assignment of plakinic acid A
Dai, Peng,Trullinger, Tony K.,Liu, Xuejun,Dussault, Patrick H.
, p. 2283 - 2292 (2007/10/03)
The first asymmetric synthesis of 1,2-dioxolane-3-acetic acids is reported. Key features include the stereoselective opening of enantiomerically enriched oxetanes by hydrogen peroxide, conversion of the resulting 4-hydroperoxy-2- alkanols to 3-alkoxy-1,2-dioxolanes, and Lewis acid mediated homologation of the latter with a thioester silyl ketene acetal. The approach is modeled on 3,5-dimethyl-5-hexadecyl-1,2-dioxolane-3-acetic acid (1a), an unnamed natural product, and an optimized strategy is applied to the synthesis of four stereoisomers of plakinic acid A (2), allowing a configurational assignment of this incompletely characterized natural product.
