4.8 Article

Enantioselective Construction of Oxa- and Aza-Angular Triquinanes through Tandem [4+1]/[3+2] Cycloaddition of Sulfur Ylides and Nitroolefins

Journal

ORGANIC LETTERS
Volume 15, Issue 3, Pages 542-545

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol303363r

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Funding

  1. National Basic Research Program of China [2011CB808603]
  2. National Natural Science Foundation of China [21232003, 21202053]
  3. CCNU

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A formal [4 + 1]/[3 + 2] cycloaddition sequence of sulfur ylides and alkene-tethered nitroolefins has been developed. The use of (R)-binol-derived chiral sulfide leads to an asymmetric process that allows the construction of oxa- and aza-angular triquinanes In good to excellent diastereo- and enantioselectivities.

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