“…The config- uration of anti - 5 was identified by comparison of its spectral data with those of the authentic sample derived from anti -2,4-pentanediol and butyryl chloride. In contrast to the reduction of β-hydroxy ketones with hydrides which produces syn 1,3-diols, − the present reaction gave anti 1,3-diols.…”
contrasting
confidence: 61%
“…The stereoselective synthesis of 1,3-dioxygenated compounds is important from the synthetic point of view, since these fragments appear in the structure of various natural products . The reduction of β-hydroxy ketones to syn 1,3-diols is usually carried out via an intermolecular hydride shift using several stoichiometric reducing agents, such as ( n -Bu) 3 B−NaBH 4 , Et 2 BOMe−NaBH 4 , terphenylboronic acid−NaBH 4 , Ti(OPr i ) 4 −NaBH 4 , catecholborane, tin hydride, DIBAL-H, and LiI−LiAlH 4 .…”
“…The config- uration of anti - 5 was identified by comparison of its spectral data with those of the authentic sample derived from anti -2,4-pentanediol and butyryl chloride. In contrast to the reduction of β-hydroxy ketones with hydrides which produces syn 1,3-diols, − the present reaction gave anti 1,3-diols.…”
contrasting
confidence: 61%
“…The stereoselective synthesis of 1,3-dioxygenated compounds is important from the synthetic point of view, since these fragments appear in the structure of various natural products . The reduction of β-hydroxy ketones to syn 1,3-diols is usually carried out via an intermolecular hydride shift using several stoichiometric reducing agents, such as ( n -Bu) 3 B−NaBH 4 , Et 2 BOMe−NaBH 4 , terphenylboronic acid−NaBH 4 , Ti(OPr i ) 4 −NaBH 4 , catecholborane, tin hydride, DIBAL-H, and LiI−LiAlH 4 .…”
In 1980, Sharpless and Katsuki discovered a system for the asymmetric epoxidation of primary allylic alcohols that utilizes Ti(OPr‐
i
)
4
, a dialkyl tartrate as a chiral ligand, and
tert
‐butyl hydroperoxide as the oxidant. Notably, this reaction exhibits high levels of enantioselectivity (usually > 90% ee). Like other metal‐catalyzed epoxidations, this reaction also proceeds under mild conditions with good chemical yield and with high regio‐ and chemoselectivity. Various aspects of this reaction, including its mechanism, early synthetic applications, and further transformations of the epoxy alcohol product, have been reviewed. In this chapter, the full scope and limitations of this reaction, its synthetic applications, and typical experimental conditions are described.
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