期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 128, 期 8, 页码 2587-2593出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja0571646
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资金
- NCI NIH HHS [R01 CA042056, R01 CA042056-22, CA 42056] Funding Source: Medline
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.
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