C-Quaternary Vinylglycinols by Metal-Catalyzed Cyclization of Allylic Bistrichloroacetimidates

被引：20

作者：

Klimovica, Kristine ^{[1
]}

Grigorjeva, Liene ^{[1
]}

Maleckis, Ansis ^{[1
]}

Popelis, Juris ^{[1
]}

Jirgensons, Aigars ^{[1
]}

机构：

[1] Latvian Inst Organ Synth, LV-1006 Riga, Latvia

来源：

SYNLETT | 2011年 / 19期

关键词：

amino alcohols; Lewis acids; palladium; cyclization; regioselectivity; VINYL AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ALPHA-VINYL; STEREOSELECTIVE ADDITION; REARRANGEMENT; DERIVATIVES; REAGENTS;

D O I：

10.1055/s-0031-1289537

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bistrichloroacetimidates derived from 2-substituted but-2-ene-1,4-diols are transformed into 4-substituted 4-vinyloxazolines in high yields and excellent regioselectivities when Lewis acids AlCl3, FeCl3, TMSOTf, BF3 center dot OEt2, and AgBF4 are used as catalysts as well as with the Pd(PPh3)(2)Cl-2/AgBF4 catalytic system. Lower regioselectivity is achieved with a neutral PdCl2(MeCN)(2) catalyst and this could be a consequence of a switch to a competitive but less selective reaction mechanism. It is demonstrated that 4-substituted 4-vinyloxazolines can be efficiently transformed to N-Boc-protected C-quaternary vinylglycinols in a one-pot procedure.

引用

页码：2849 / 2851

页数：3

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