Activation of Fmoc-Protected N,O-Acetals Using Trimethylsilyl Halides: Mechanistic and Synthetic Studies

被引：6

作者：

Boaz, Nicholas C. ^{[1
]}

Bair, Nathaniel C. ^{[1
]}

Le, Thanh T. ^{[1
]}

Peelen, Timothy J. ^{[1
]}

机构：

[1] Lebanon Valley Coll, Dept Chem, Annville, PA 17003 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 11期

关键词：

N-ACYLIMINIUM IONS; ACYL IMINIUM IONS; LEWIS-ACID; INTERMOLECULAR ADDITION; ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; NUCLEOPHILES; DERIVATIVES; ALKYLATION; CHEMISTRY;

D O I：

10.1021/ol100494z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trimethylsilyl halide activation of Fmoc-protected N,O-acetals yields reactive intermediates capable of efficiently adding to a variety of enamines. NMR studies have provided evidence that a stable halomethyl carbamate intermediate forms in solution. Good yields are obtained over a broad range of enamine nucleophiles encompassing both cyclic and acyclic ketone-derived and aldehyde-derived enamines. Preliminary studies suggest that the enamine additions occur through a concerted, S(N)2-type mechanism.

引用

页码：2464 / 2467

页数：4

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