Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis
نویسندگان
چکیده
A variety of ortho,ortho'-disubstituted hydrobenzoin derivatives are readily accessible through a directed ortho,ortho'-dimetalation strategy in which the alcohol functions in hydrobenzoin are deprotonated by n-BuLi and the resulting lithium benzyl alkoxides serve as directed metalation groups. The optimization and scope of this reaction are discussed, and the utility of this process is demonstrated in the one-pot preparation of a number of chiral diols as well as a short synthesis of the chiral ligand Vivol.
منابع مشابه
Bidirectional metalation of hydrobenzoin: direct access to new chiral ligands and auxiliaries.
A bidirectional ortho metalation of the readily available chiral diol hydrobenzoin has been developed that provides direct access to new ortho-functionalized hydrobenzoin derivatives. This one-pot procedure should broaden the utility of hydrobenzoin as an auxiliary and ligand in asymmetric synthesis.
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