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Start Over Author "Aleksandra Murre" Topic 010405 organic chemistry
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1. Diastereoselective [2,3]-Sigmatropic Rearrangement of N-Allyl Ammonium Ylides

Author

Kristin Erkman, Tõnis Kanger, Aleksandra Murre, Sandra Kaabel, and Ivar Järving

Subjects
chemistry.chemical_compound, Chiral auxiliary, 010405 organic chemistry, Chemistry, 2,3-sigmatropic rearrangement, Product (mathematics), Organic Chemistry, Ammonium, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Catalysis, 0104 chemical sciences
Abstract

A rapid and diastereoselective method was developed for the [2,3]-sigmatropic rearrangement of N-allyl ammonium ylides, affording products in up to 95% isolated yields and up to 97:3 dr; most of the desired products were formed within 1 minute. For the asymmetric reaction, a chiral auxiliary was introduced to the starting compound, affording the rearrangement product with high diastereoselectivities.

Published
2019

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