Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 34, Pages 11895-11902Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b05619
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Funding
- European Union (Marie Curie ITN SubiCat) [PITN-GA-2013-607044]
- ERC under the European Union/ERC [279850]
- Royal Society
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A tandem relay catalytic protocol using both Pd and isothiourea catalysis has been developed for the enantioselective synthesis of alpha-amino acid derivatives containing two stereogenic centers from readily accessible N,N-disubstituted glycine aryl esters and allylic phosphates. The optimized process uses a bench-stable succinimide-based Pd precatalyst (FurCat) to promote Pd-catalyzed allylic ammonium. salt generation from the allylic phosphate and the glycine aryl ester. Subsequent in situ enantioselective [2,3]-sigmatropic rearrangement catalyzed by the isothiourea benzotetramisole forms syn-alpha-amino acid derivatives with high diastereo- and enantioselectivity. This methodology is most effective using 4-nitrophenylglycine esters and tolerates a variety of substituted cinnamic and styrenyl allylic ethyl phosphates. The use of challenging unsymmetrical N-allyl-N-methylglycine esters is also tolerated under the catalytic relay conditions without compromising stereoselectivity.
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