4.5 Article

Asymmetric Formal [3+2] Cycloaddition Reaction of Succinaldehyde and Nitroalkene Catalyzed by Diphenylprolinol Silyl Ether

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 20, Pages 4320-4324

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500623

Keywords

Organocatalysis; Michael addition; Domino reactions; Cycloaddition; Nitro compounds

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan [23105010]
  2. Grants-in-Aid for Scientific Research [14J03546, 25620074] Funding Source: KAKEN

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The enantioselective domino Michael/Henry reaction of nitroalkenes with succinaldehyde was found to proceed efficiently upon using diphenylprolinol silyl ether as the organocatalyst. The reaction affords cis-disubstituted nitropen-tenes with excellent diastereoselectivities and enantioselectivities after treatment of the Michael product with Ac2O and pyridine.

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