Journal
ORGANIC LETTERS
Volume 24, Issue 49, Pages 9017-9022Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03645
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Funding
- National Natural Science Foundation of China
- Chinese Universities Scientific Fund
- Scientific Fund of North-west AF University
- [22171229]
- [21722206]
- [21572182]
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In this study, a catalytic asymmetric intramolecular vinylogous aldol reaction using dual organocatalysts was described, allowing for the convergent synthesis of ortho-fused tricyclic diketones with excellent enantioselectivities and diastereoselectivities. Notably, the reaction selectively generates three consecutive stereogenic carbon centers, including a quaternary one. Density functional theory calculations revealed that the enhanced enantioselectivity was facilitated by a transannular hydrogen bonding between the protonated quinuclidine moiety of the chiral aminocatalyst and the diketone fragment of the substrate.
Herein, we describe a catalytic asymmetric intramolecular vinylogous aldol reaction by taking advantage of dual organocatalysts, which enables convergent synthesis of ortho-fused tricyclic diketones in excellent enantioselectivities and diastereoselectivities. Noteworthy is that the reaction stereoselectively forges three consecutive stereogenic carbon centers including a quaternary one. Density functional theory calculations reveal that the enantioselectivity was facilitated by a transannular hydrogen bonding between the protonated quinuclidine moiety of the chiral aminocatalyst and the diketone fragment of the substrate.
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