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Published on: August 16, 2018
Tethered Silanoxymercuration of Allylic Alcohols
Anand H Shinde1, Shyam Sathyamoorthi1
1Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.
Abstract:
We present the first examples of tethered olefin functionalization reactions using a silanol auxiliary. A range of allylic alcohols are readily condensed with di-tert-butylsilyl bis(trifluoromethanesulfonate) to form allylic silanols. When treated with Hg(OTf)2 and NaHCO3, these silanols easily transform into cyclic silanediol organomercurial compounds. In most cases, the reactions are exquisitely diastereoselective. The scale can be increased more than 10-fold without a loss of yield and selectivity. We demonstrate that the silanediols are versatile synthons for a variety of further reactions.
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