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 %).
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页数：4
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