Journal
ORGANIC LETTERS
Volume 21, Issue 22, Pages 9119-9123Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03509
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [26105721, 16H06217]
- Amano Institute of Technology scholarship
- 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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