Abstract 1,2‐Epoxy‐3‐methylpentanes (1) of different diastereoisomeric compositions were polymerized using anionic (tert‐BuOK, KOH), stereospecific (ZnEt2/H2O, ZnEt2/MeOH), or stereoelective (ZnEt2/R(−) 3,3‐dimethyl‐1,2‐butanediol (R( − ) DMBD)) catalysts. In all the cases a preferential incorporation of the (2R,3S) diastereoisomer in the polymer chain was observed. With anionic and coordinated anionic achiral catalysts the election was low but significant, whereas with the chiral ZnEt2/R( − ) DMBD system, in the case of the polymerization of the (2RS,3S) monomer, the election was high and corresponded to a stereoelectivity ratio of r = 4, the highest one obtained up to now for oxiranes. The observed effects are due to the presence of a chiral centre in the side chain of the monomer.
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Goguelin et al. (1979) studied this question.
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