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Synthesis of enantioenriched 2,2-disubstituted pyrrolidines via sequential asymmetric allylic alkylation and ring contraction

Goldstein, Elizabeth L. and Takada, Hirokazu and Sumii, Yuji and Baba, Katsuaki and Stoltz, Brian M. (2022) Synthesis of enantioenriched 2,2-disubstituted pyrrolidines via sequential asymmetric allylic alkylation and ring contraction. Tetrahedron, 123 . Art. No. 132940. ISSN 0040-4020. doi:10.1016/j.tet.2022.132940.

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The synthesis of a variety of enantioenriched 2,2-disubstituted pyrrolidines is described. A stereogenic quaternary center is first formed utilizing an asymmetric allylic alkylation reaction of a benzyloxy imide, which can then be reduced to a chiral hydroxamic acid. This compound can then undergo a thermal “Spino” ring contraction to afford a carbamate protected 2,2-disubstituted pyrrolidine stereospecifically. These pyrrolidines can be further advanced to enantioenriched indolizidine compounds. This reaction sequence allows access to new molecules that could be useful in the development of pharmaceutical agents.

Item Type:Article
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URLURL TypeDescription
Goldstein, Elizabeth L.0000-0002-2208-6090
Takada, Hirokazu0000-0003-3452-6070
Sumii, Yuji0000-0003-3900-1089
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:This work was supported by the NIH under NIH-NIGMS (R01GM080269 and R35GM145239) and the Heritage Medical Research Institute Investigator Program. E.L.G recognizes the NSF for a predoctoral research fellowship (No. DGE-1745301). Dr. David VanderVelde and Dr. Scott Virgil are acknowledged for assistance with structural determination and characterization.
Group:Heritage Medical Research Institute
Funding AgencyGrant Number
Heritage Medical Research InstituteUNSPECIFIED
NSF Graduate Research FellowshipDGE-1745301
Record Number:CaltechAUTHORS:20221114-800492800.1
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ID Code:117852
Deposited By: Research Services Depository
Deposited On:29 Nov 2022 17:27
Last Modified:29 Nov 2022 17:55

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