Hydroxyselenylation and Tethered Silanoxyselenylation of Allylic Silanols

被引：11

作者：

Joshi, Harshit ^{[1
]}

Sathyamoorthi, Shyam ^{[1
]}

机构：

[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66047 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 07期

基金：

美国国家卫生研究院;

关键词：

N-PHENYLSELENOPHTHALIMIDE; ORGANOSELENIUM CHEMISTRY; ALCOHOLS; HYDROXY; OLEFINS; SELENOLACTONIZATION; TRANSFORMATION; REAGENT; ESTERS; ACIDS;

D O I：

10.1021/acs.joc.2c00119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: We present protocols for the highly regioselective hydroxyselenylation and silanoxyselenylation of allylic silanols. N- (Phenylseleno)phthalimide acts as the selenylating agent for both transformations. Under basic conditions, hydroxyselenylation proceeds with >20:1 regioselectivity, and the products are valuable synthons for further transformations. We show that the silanol plays a critical role in maintaining the yield and regioselectivity of this reaction. Surprisingly, under acidic conditions, the hydroxyselenylation pathway is blocked, and products of a tethered silanoxyselenylation are exclusive.

引用

页码：5017 / 5028

页数：12

共 32 条

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