Gold(I)-catalyzed synthesis of dihydropyrans

被引：184

作者：

Sherry, Benjamin D. ^{[1
]}

Maus, Lisa ^{[1
]}

Laforteza, Brian Ngo ^{[1
]}

Toste, F. Dean ^{[1
]}

机构：

[1] Univ Calif Berkeley, Ctr New Direct Organ Synth, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 25期

关键词：

D O I：

10.1021/ja061344d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A trinuclear gold(I)-oxo complex, [(Ph3PAu)3O]BF4, serves as the catalyst for the stereocontrolled synthesis of 2-hydroxy-3,6-dihydropyrans from propargyl vinyl ethers. Importantly, the rearrangement proceeds with excellent diastereoselectivity, and the rearrangement of chiral nonracemic propargyl vinyl ethers proceeds with excellent chirality transfer to furnish enantioenriched pyrans. Additionally, the reaction is amenable to the synthesis of spiroketals from appropriately functionalized precursors. In this case, from a linear precursor, in a single step, the bicyclic spiroketal framework is established with complete stereocontrol over three centers and an alkene functional group in the product. Copyright © 2006 American Chemical Society.

引用

页码：8132 / 8133

页数：2

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