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Enantioselective synthesis of gem-disubstituted N-Boc diazaheterocycles via decarboxylative asymmetric allylic alkylation

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)
Related URLs:
URLURL TypeDescription
https://www.acs.org/content/acs/en/meetings/national-meeting.htmlOrganizationConference Website
http://resolver.caltech.edu/CaltechAUTHORS:20181106-111914131Related ItemJournal Article
ORCID:
AuthorORCID
Sun, Alexander0000-0001-6639-4469
Stoltz, Brian Mark0000-0001-9837-1528
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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