Sun, Alexander and Stoltz, Brian Mark (2019) Enantioselective synthesis of gem-disubstituted N-Boc diazaheterocycles via decarboxylative asymmetric allylic alkylation. In: 257th ACS National Meeting & Exposition, 31 March - 4 April 2019, Orlando, FL. https://resolver.caltech.edu/CaltechAUTHORS:20190325-092717158
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Abstract
An enantioselective synthesis of diverse N4-Boc-protected a,a-disubstituted piperazin-2-ones using the palladiumcatalyzed decarboxylative allylic alkylation reaction has been achieved. Using a chiral Pd-catalyst derived from an electron deficient PHOX ligand, chiral piperazinones are synthesized in high yields and enantioselectivity. The chiral piperazinone products can be deprotected and reduced to valuable gem-disubstituted piperazines. This reaction is further extended to enable the enantioselective synthesis of a,a-disubstituted tetrahydropyrimidin-2-ones, which are hydrolyzed into corresponding chiral b2,2-amino acids.
Item Type: | Conference or Workshop Item (Paper) | |||||||||
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Additional Information: | © 2019 American Chemical Society. | |||||||||
Record Number: | CaltechAUTHORS:20190325-092717158 | |||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20190325-092717158 | |||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
ID Code: | 94105 | |||||||||
Collection: | CaltechAUTHORS | |||||||||
Deposited By: | Tony Diaz | |||||||||
Deposited On: | 25 Mar 2019 16:49 | |||||||||
Last Modified: | 11 Oct 2019 18:07 |
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