54371-12-9Relevant articles and documents
N/N/O versus N/O/O and N/O amino isoborneols in the enantioselective ethylation of benzaldehyde
de las Casas Engel, Tomas,Maroto, Beatriz Lora,Martinez, Antonio Garcia,de la Moya Cerero, Santiago
, p. 269 - 272 (2008)
Enantiopure 10-(4-methylpiperazin-1-yl)isoborneol, a N/N/O-tridentate chiral diamino isoborneol, has been obtained from enantiopure ketopinic acid and its catalytic activity (as chiral ligand in the enantioselective addition of diethylzinc to benzaldehyde) measured and compared with the previously reported data for related N/N/O, N/O/O, and N/O isoborneols. It is demonstrated that the pentacoordinated-zinc Oppolzer's model for transition states is useful for explaining the catalytic behavior of N/N/O-tridentate ligands. In such cases, stable syn- or anti-type transition states can be proposed depending on the catalyst's conformational flexibility.
Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones
Dalinger, Alexander I.,Kalinin, Mikhail A.,Kuranov, Sergey O.,Munkuev, Aldar A.,Okhina, Alina A.,Ottenbacher, Roman V.,Patrusheva, Oxana S.,Ponomarev, Konstantin Y.,Rogachev, Artem D.,Salakhutdinov, Nariman F.,Suslov, Evgeniy V.,Vatsadze, Sergey Z.,Volcho, Konstantin P.
, (2021/12/20)
A number of new chiral bispidines containing monoterpenoid fragments have been ob-tained. The bispidines were studied as ligands for Ni-catalyzed addition of diethylzinc to chalcones. The conditions for chromatographic analysis by HPLC-UV were developed,
Direct Decarboxylative Functionalization of Carboxylic Acids via O-H Hydrogen Atom Transfer
Na, Christina G.,Ravelli, Davide,Alexanian, Erik J.
supporting information, p. 44 - 49 (2020/01/22)
Decarboxylative functionalization via hydrogen atom transfer offers an attractive alternative to standard redox approaches to this important class of transformations. Herein, we report a direct decarboxylative functionalization of aliphatic carboxylic acids using N-xanthylamides. The unique reactivity of amidyl radicals in hydrogen atom transfer enables decarboxylative xanthylation under redox-neutral conditions. This platform provides expedient access to a range of derivatives through subsequent elaboration of the xanthate group.
Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand
Wu, Hsyueh-Liang,Wu, Ping-Yu,Cheng, Ying-Ni,Uang, Biing-Jiun
, p. 2656 - 2665 (2016/05/10)
In this article, the design and synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding alcohols in high yields and enantioselectivities. The role of the mercapto group in the highly enantioselective 1,2-addition reaction of organozincs to aldehyde is also discussed.
