4.8 Article

Chemoselective Umpolung of Enals for Asymmetric Homoenolate Cross-Annulation of Enals and Aldehydes Catalyzed by N-Heterocyclic Carbene

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ORGANIC LETTERS
卷 21, 期 22, 页码 9119-9123

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03509

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  1. Ministry of Education, Culture, Sports, Science and Technology, Japan [26105721, 16H06217]
  2. Amano Institute of Technology scholarship
  3. Grants-in-Aid for Scientific Research [16H06217, 26105721] Funding Source: KAKEN

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An asymmetric homoenolate cross-annulation of enals and aldehydes with high enantioselectivity is realized by NHC-catalyzed chemoselective umpolung of enals. The reaction proceeds in a highly chemoselective manner, selectively generating the conjugated Breslow intermediates from enals rather than aldehydes, enabling the homoenolate addition of enals to aldehydes in preference to competing acyl anion-mediated reactions. Enantioenriched substituted gamma-butyrolactones are formed in good yields with high enantioselectivities.

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