期刊
ACS CATALYSIS
卷 6, 期 2, 页码 661-665出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b02403
关键词
asymmetric catalysis; rhodium; arylation; cyclic ketimine; P-olefin ligand; alpha-amino acid
资金
- National Science Foundation of China [21325209, 21472205]
- Shanghai Municipal Committee of Science and Technology (Program of Shanghai Academic Research Leader) [14XD1404400]
A new class of open-chain chiral phosphite based hybrid olefin ligands has been developed and utilized in Rh-catalyzed asymmetric arylation of 1,2,5-thiadiazolidine 1,1-dioxide type cyclic ketimines. The reactions generate quaternary carbon-containing, gem-diaryl-substituted sulfahydantoins and 4-ethoxy-2,3-dihydro-1,2,S-thiadiazole 1,1-dioxides with excellent enantioselectivities under exceptionally mild and user-friendly conditions using a H-8-binol-derived phosphite-olefin ligand. The method is useful in offering efficient and convenient synthesis of enantioriched alpha,alpha-diaryl-alpha-amino acid amides and nitrogen-containing heterocycles. Furthermore, by taking advantage of the protocol, the first enantioselective synthesis of BACE1 inhibitor (R)-iminohydantoin has been accomplished.
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