Bistrimethylsilylpropargylic ether:: A versatile ambident synthon to access substituted allenyne ethers and α-substituted bispropargylic alcohols

被引：24

作者：

Brossat, Maude

Heck, Marie-Pierre

Mioskowski, Charles

机构：

[1] CEA Saclay, Serv Chim Bioorgan Marqueage, IBiTec S, F-91191 Gif Sur Yvette, France

[2] Univ Strasbourg 1, Fac Pharm, Lab Synth, F-67401 Illkirch Graffenstaden, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 15期

关键词：

SOFT ACIDS; REARRANGEMENT; REACTIVITY; PRINCIPLE; BASES; HARD;

D O I：

10.1021/jo0709753

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactivity of 1,5-bis(trimethylsilyl)propargylic ethers 3 toward bases and electrophiles was investigated. Bispropargylic ethers 4, substituted allenyne ethers 6-8, and alpha-substituted bispropargylic ethers 9 were prepared in good yields, respectively, by protodesilylation, isomerization, or metalation/alkylation of bispropargylic protected alcohol 3. The ambident behavior of metalated synthon 3 was discussed and rationalized. Removal of the protecting groups of 9 easily afforded useful alpha-substituted bispropargylic alcohol.

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页码：5938 / 5941

页数：4

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