Organocatalytic route to the enantioselective synthesis of syn/ anti-α-hydrazino-γ-fluoro alcohols

被引：0

作者：

Khonde, Nilesh S. ^{[1
,2
]}

Said, Madhukar S. ^{[1
,2
]}

Danve, Shivam S. ^{[1
]}

Kumar, Pradeep ^{[1
,2
]}

机构：

[1] CSIR Natl Chem Lab, Div Organ Chem, Dr Homi Bhabha Rd, Pune 411008, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

来源：

TETRAHEDRON LETTERS | 2024年 / 145卷

关键词：

Organocatalyst; HWE olefination; alpha-Fluorination; alpha-Amination; Enantioselectivity; Diastereoselectivity; CATALYZED ASYMMETRIC AMINATION; ISOSTERES; ALDEHYDES;

D O I：

10.1016/j.tetlet.2024.155179

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general organocatalytic method has been developed for the asymmetric synthesis of alpha-hydrazino-gamma-fluoro alcohols, a precursor to syn/anti-1,3-fluoro amines. The strategy employs alpha-fluorination catalyzed by prolinederived catalyst, (S)-alpha,alpha-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether followed by Horner-Wadsworth-Emmons (HWE) olefination of aldehydes, and proline-catalyzed alpha-amination as the key steps. The title compounds showed excellent diastereoselectivity (up to 99:1) and enantioselectivity (up to 99 %).

引用

页数：4

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