期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 12, 页码 4492-4495出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja501005g
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资金
- NSF [CHE-1112397, CHE-030089]
- Robert A. Welch Foundation [A-1280]
- ACS PRF [52801-ND4]
- NIH [GM 052964]
- U.S. Department of Education (GAANN Fellowship)
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1112397] Funding Source: National Science Foundation
alpha,beta-Unsaturated acylammonium salts, generated in situ from commodity acid chlorides and a chiral isothiourea organocatalyst, comprise a new and versatile family of chiral dienophiles for the venerable Diels-Alder (DA) cycloaddition. Their reactivity is unveiled through a highly diastereo- and enantioselective Diels-Alder/lactonization organocascade that generates cis- and trans-fused bicyclic gamma- and delta-lactones bearing up to four contiguous stereocenters. Moreover, the first examples of DA-initiated, stereodivergent organocascades are described delivering complex scaffolds found in bioactive compounds. The origins of stereoselectivity are rationalized through computational studies. In addition, the utility of this methodology is demonstrated through a concise approach to the core structure of glaciolide and formal syntheses of fraxinellone, trisporic acids, and trisporols.
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