Replacement of HMPA in Samarium Diiodide Promoted Cyclizations and Reactions of Organolithium Compounds

被引：39

作者：

Berndt, Mathias ^{[1
]}

Hoelemann, Alexandra ^{[1
]}

Niermann, Andre ^{[1
]}

Bentz, Christoph ^{[1
]}

Zimmer, Reinhold ^{[1
]}

Reissig, Hans-Ulrich ^{[1
]}

机构：

[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 07期

关键词：

Lewis bases; Phosphorus; Samarium; Radicals; Cyclization; Lithium; STEREOSELECTIVE-SYNTHESIS; REDUCTIVE CYCLIZATIONS; CARBONYL-COMPOUNDS; ORGANIC HALIDES; REDUCING POWER; SMI2; DERIVATIVES; GAMMA; KETYLS; MILD;

D O I：

10.1002/ejoc.201101830

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tripyrrolidinophosphoric acid triamide (TPPA) can replace carcinogenic HMPA as a Lewis basic additive in many reactions involving samarium ketyls. In most cases, yields and selectivities of cyclizations of (het)aryl, alkenyl, and alkynyl ketones are similar. TPPA is also a good substitute of HMPA in the O-silylation of an ester enolate and in reactions oflithiated 1,3-dithiane. All these results clearly demonstrate that in many cases the use of HMPA can be avoided.

引用

页码：1299 / 1302

页数：4

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