Organocatalyzed Enantioselective [2 + 2] Cycloaddition of C,N‑Cyclic Ketimines and Allenoates

We report a novel enantioselective and regioselective [2 + 2] cycloaddition of allenoate and C,N-cyclic ketimine catalyzed by a quinidine derivative. The methodology enables the synthesis of fused tricyclic azetidines with a quaternary stereogenic center exhibiting high enantioselectivities. The bro...

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Bibliographic Details
Published inOrganic letters Vol. 26; no. 1; pp. 225 - 230
Main Authors Liu, Xinyu, Zhu, Fangfang, Ajitha, Manjaly J., Zhang, Yunfeng, Huang, Kuo-Wei, Li, Dehai, Wang, De
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 12.01.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AZETIDINES
IMINES
BONDS
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Summary:We report a novel enantioselective and regioselective [2 + 2] cycloaddition of allenoate and C,N-cyclic ketimine catalyzed by a quinidine derivative. The methodology enables the synthesis of fused tricyclic azetidines with a quaternary stereogenic center exhibiting high enantioselectivities. The broad range of substrates demonstrates the generality of the protocol, and the resulting functional products can be easily converted to a variety of valuable synthons. To elucidate the plausible reaction mechanism and how the catalyst affects absolute stereocontrol over the products, we conducted the corresponding density functional theory (DFT) calculations.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03848