烯丙醇的硅烷氧基汞化反应。
Tethered Silanoxymercuration of Allylic Alcohols.
机构信息
Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.
出版信息
Org Lett. 2020 Nov 6;22(21):8665-8669. doi: 10.1021/acs.orglett.0c03257. Epub 2020 Oct 23.
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--butylsilyl bis(trifluoromethanesulfonate) to form allylic silanols. When treated with Hg(OTf) and NaHCO, 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.
摘要
我们展示了首例使用硅醇辅助物进行的束缚烯烃官能化反应。一系列烯丙醇很容易与二--丁基硅基双（三氟甲磺酸酯）缩合形成烯丙基硅醇。用 Hg(OTf) 和 NaHCO 处理时，这些硅醇很容易转化为环状硅烷二醇有机汞化合物。在大多数情况下，反应具有极好的非对映选择性。反应的规模可以增加 10 倍以上，而不会影响产率和选择性。我们证明了硅烷二醇是多种进一步反应的多功能合成子。
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