Highly enantioselective syntheses of heterocycles via intramolecular Ir-catalyzed allylic amination and etherification

被引：138

作者：

Welter, C ^{[1
]}

Dahnz, A ^{[1
]}

Brunner, B ^{[1
]}

Streiff, S ^{[1
]}

Dubon, P ^{[1
]}

Helmchen, G ^{[1
]}

机构：

[1] Heidelberg Univ, Chirurg Klin, Inst Organ Chem, D-69120 Heidelberg, Germany

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 07期

关键词：

D O I：

10.1021/ol047351t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective Ir-catalyzed intramolecular allylic aminations and etherifications are described. Up to 97% ee was achieved using catalysts prepared by in situ activation of mixtures of phosphorus amidites and [Ir(COD)Cl](2)- Sequential aminations of bis-allylic carbonates, involving an inter- followed by an intramolecular reaction, gave trans-N-benzyl-2,5-divinylpyrrolidine and trans- N-benzyl-2,6-divinylpiperidine with >= 99% ee. New phosphorus amidites as well as improved conditions for intermolecular aminations are reported.

引用

页码：1239 / 1242

页数：4

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