| Predicate |
Object |
| assignee |
http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_f8c0982b0f02b1ed6d20a315370a3a3a |
| classificationCPCInventive |
http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D491-052
http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D263-14 |
| classificationIPCInventive |
http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D491-052
http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D491-04 |
| filingDate |
2015-02-27-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor |
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_47287e03ec4e011f0481d7cd8905bbbd |
| publicationDate |
2015-09-03-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber |
WO-2015131100-A1 |
| titleOfInvention |
Ligand-controlled c(sp3)-h arylation and olefination in synthesis of unnatural chiral alpha amino acids |
| abstract |
The use of ligands to tune the reactivity and selectivity of transition metal-catalysts for C(-sp3)-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp3)-H arylation using pyridine and quinoline derivatives: the former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of β-Ar-p-Ar ' -cc-amino acids with excellent levels of diastereoselectivity (d.r. > 20:1). Both configurations of the β-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp3)-H olefination of a protected alanine. |
| isCitedBy |
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-11021427-B2
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-106995483-B
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-112312902-A
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-112312902-B
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-110121492-B
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-110121492-A
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2018080897-A1
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/JP-7122255-B2
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-10759743-B2
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-106995483-A
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2022223805-A1
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2022238565-A2
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-4089102-A1
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-4079748-A1
http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2019204477-A1 |
| priorityDate |
2014-02-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type |
http://data.epo.org/linked-data/def/patent/Publication |