- An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction
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A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction.Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate.Upon desilylation, this compound undergoes a Payne-type rearrangement.Nucleophilic epoxide-opening then provides an erythro-2,3-diol.The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel.Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures.Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, -N3, -OAc, -CN, halides as well as carbon nucleophiles and hydride.
- Ko, Soo Y.,Malik, Majbeen,Dickinson, A. Frances
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- Synthesis of Carbohydrates and Related Polyhydroxylated Compounds Employing Asymmetric Dihydroxylation. 1. An Access to Erythro-diols
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Asymmetric dihydroxylation provides an easy access to tetrose: threose directly from the (E)-olefin 1, and erythrose via an irreversible Payne-type rearrangement - opening process of the threitol cyclic sulfate 5.
- Ko, Soo Y.,Malik, Majbeen
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p. 4675 - 4678
(2007/10/02)
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