Journal
ORGANIC LETTERS
Volume 24, Issue 38, Pages 6957-6961Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02759
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Funding
- Fundamental Research Funds for the Central Universities [2022CDJXY-025, 2020CDJQY-Z002]
- National Natural Science Foundation of China [21871033, 21922102, 22101037]
- Venture & Innovation Support Program for Chongqing Overseas Returnees [cx2021091]
- Open Project of Key Laboratory of Prevention and Treatment of Cardiovascular and Cerebrovascular Diseases, Ministry of Education [XN202008]
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A sequence of reactions has been developed to synthesize bicyclic indolizidines with bridgehead aza-quaternary stereocenters from chiral cyclopropyl ketones. The reactions proceed with excellent chirality transfer, tolerating various functional groups and producing products with high enantiomeric purities.
A sequence of nucleophilic ring opening of cyclopropyl ketones, N-quaternization, deprotonation, and [2,3]-sigmatropic rearrangement of ammonium ylides has been developed. This method enables efficient synthesis of bicyclic indolizidines bearing bridgehead aza-quaternary stereocenters from easily available chiral cyclopropyl ketones. The reactions proceeded with an excellent level of chirality transfer and tolerated various functional groups, providing a diverse array of allenyl- or allyl-substituted indolizidines with high enantiomeric purities (up to >99% ee).
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