Diastereoselective Diels-Alder reactions of N-sulfonyl-1-aza-1,3-butadienes with optically active enol ethers: An asymmetric variant of the 1-azadiene Diels-Alder reaction

被引：0

作者：

Clark, Ryan C. ^{[1
]}

Pfeiffer, Steven S. ^{[1
]}

Boger, Dale L. ^{[1
]}

机构：

[1] Department of Chemistry, Skaggs Institute for Chemical Biology, Scripps Research Institute, 10550 North Torrey Pines Road, San Diego, CA 92037, United States

来源：

Journal of the American Chemical Society | 2006年 / 128卷 / 08期

关键词：

The first detailed study of a room-temperature asymmetric Diels-Alder reaction of N-sulfonyl-1-aza-1,3-butadienes is reported enlisting a series of 19 enol ethers bearing chiral auxiliaries, with many providing highly diastereoselective (endo and facial diastereoselection) reactions, largely the result of an exquisitely organized [4+2] cycloaddition transition state. Three new, readily accessible, and previously unexplored auxiliaries rationally emerged from the studies and provide remarkable selectivities (two of these give 49:1 endo:exo and 48:1 facial selectivity) that promise to be useful in systems beyond those detailed. © 2006 American Chemical Society;

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摘要：

Journal article (JA)

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页码：2587 / 2593