Taming Tethered Nitreniums for Alkene Functionalization Reactions

被引：0

作者：

Silver, Raju ^{[1
]}

Nirpal, Appasaheb K. ^{[1
]}

Sathyamoorthi, Shyam ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 20期

基金：

美国国家卫生研究院;

关键词：

N-ACYLNITRENIUM IONS; SHARPLESS ASYMMETRIC AMINOHYDROXYLATION; ELECTROPHILIC AROMATIC-SUBSTITUTION; CATALYZED INTRAMOLECULAR AMIDATION; MEDIATED ALKYNE AMIDATION; OXIDATIVE CYCLIZATION; OLEFIN AMIDOHYDROXYLATION; FORMAL SYNTHESIS; AZASPIROCYCLIZATION; AZIRIDINATION;

D O I：

10.1021/acs.joc.4c01886

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present the first examples of amino-trifluoroacetoxylations of alkenes using N-alkoxy carbamate tethers. Hypervalent iodine oxidants mediate this transformation, providing a "green" alternative to existing intramolecular amino-hydroxylation protocols which use toxic metals such as osmium. In all cases examined, the reaction is regioselective and stereospecific, with the geometry of the starting alkene controlling the diastereomeric outcome. By analogy to prior art and from our own observations, we posit that a transient nitrenium species serves as a key intermediate.

引用

页码：15352 / 15357

页数：6

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