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• W2011506410 abstract "Starting from D-mannitol, we have prepared several C(2)-symmetric ethanotethered bis(alpha,beta-butenolides) and studied their [2+2] photocycloaddition reaction with ethylene. The protective groups of the central diol unit have a noticeable influence on the facial selectivity of the cycloaddition, the bis(trimethylsilyloxy) derivatives showing the highest diastereoselectivity. A theoretical conformational analysis of the substrates in the ground state is in good agreement with the diastereofacial selectivity experimentally observed. The bis(photocycloadducts) have been converted into the enantiopure cyclobutanes formally derived from the photoreaction of ethylene with gamma-hydroxymethyl-alpha,beta-butenolide, in which only a moderate facial selectivity had been previously found. As an application of these studies, we have developed a highly efficient and stereoselective synthesis of (+)-grandisol." @default.
• W2011506410 created "2016-06-24" @default.
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• W2011506410 date "2003-02-20" @default.
• W2011506410 modified "2023-09-30" @default.
• W2011506410 title "<i>C</i>₂-Symmetric Enantiopure Ethanotethered Bis(α,β-butenolides) as Templates for Asymmetric Synthesis. Application to the Synthesis of (+)-Grandisol¹" @default.
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• W2011506410 doi "https://doi.org/10.1021/jo026705w" @default.
• W2011506410 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/12636414" @default.
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