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

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 al...

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Published inOrganic letters Vol. 21; no. 22; pp. 9119 - 9123
Main Authors Ide, Ryuji, Kyan, Ryuji, Phuc Le, Thien, Kitagawa, Yuya, Sato, Kohei, Mase, Nobuyuki, Narumi, Tetsuo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.11.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
INTERMOLECULAR STETTER REACTION
COOPERATIVE CATALYSIS
ACID
STEREOSELECTIVE-SYNTHESIS
SALTS
GAMMA-BUTYROLACTONES
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Summary: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 γ-butyrolactones are formed in good yields with high enantioselectivities.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03509