Abstract
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.
Original language | English (US) |
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Pages (from-to) | 225-230 |
Number of pages | 6 |
Journal | Organic Letters |
Volume | 26 |
Issue number | 1 |
DOIs | |
State | Published - Jan 12 2024 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry