Diethyl cyclic carbonate ring opening with

Chiral allylic cyclic carbonates such as 551 or 552 undergo excellent regioselective alkylation reactions with soft nucleophiles in the presence of palladium(O) in refluxing THF to provide ( )-allylic alcohols. The reaction of 4-0-benzyl-2,3-isopropylidene-L-threose (167) with the appropriate ylid, followed by deprotection of the isopropylidene ring with acidic resin and cyclic carbonate formation, provides a good overall yield of either 551 or 552. Ring opening with diethyl malonate in the presence of tetrakis(triphenylphosphine)palladium(0) provides in excellent yield the allylic alcohols 553 or 554, where the diastereoselectivity exceeds 99%. This reaction represents an efficient method of 1,3-chirality transfer [180] (Scheme 122). 

Several decades later, in the early 1930s, work (and interest) once more revived on aliphatic polycarbonates when Carothers and van Natta were able to produce low-melting, low-molecular-weight, microcrystalline aliphatic polycarbonates via two different synthetic pathways [27]. The first method was the transesterification of aliphatic dihydroxylic compounds with diethyl carbonate. The second approach was via ring-opening polymerization of cyclic carbonates of aliphatic dihydroxylic... 

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