Chiral acetals in organic synthesis: Regioselective synthesis of 2-and 3-hydroxy acetals from 2,3-olefinic acetals. Reinvestigation and further applications
Achiral as well as chiral 2,3-olefinic acetals are converted into 2- and 3- hydroxy acetals via LAH reduction of the corresponding epoxides and via bromohydrins followed by TBTH reductions respectively. Synthesis of 1,3-diones is described. Compounds from chiral systems are further utilized for asymmetric synthesis.
Vankar, Yashwant D.,Reddy, M. Venkatram,Chaudhuri, Narayan C.
REGIOSELECTIVE REDUCTIONS OF 2,3-EPOXY ACETALS WITH ZINC-CHLOROTRIMETHYLSILANE AND LITHIUM ALUMINIUM HYDRIDE: CONVENIENT SYNTHESIS OF 1,2 AND 1,3-DIONES
A variety of 2,3-epoxy acetals have been found to undergo regioselective reductions with zinc-chlorotrimethylsilane and lithium aluminium hydride to give 2-hydroxy and 3-hydroxy acetals respectively.Their oxidation followed by hydrolysis furnished the corresponding 1,2- and 1,3-diones in good yields.
Vankar, Yashwant D.,Chaudhuri, Narayan C.,Rao, C. Trinadha
p. 551 - 554
(2007/10/02)
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