15754-20-8Relevant articles and documents
Synthesis of 14C-labeled S-(-)-1-phenylethylamine and its application to the synthesis of [14C] CI-1021, a potential antiemetic agent(1)
Zhang, Yinsheng
, p. 1087 - 1093 (2000)
S-(-)-1-[U-ring- 14C]phenylethylamine 3 was synthesized through the enantioselective borane reduction of E-[U-ring-14C]acetophenone oxime methyl ether derived from [U-ring-14C]acetophenone. The overall radiochemical yield was 66.7%. The enantiomeric excess (ee) was 96.60%. Coupling the labeled amine 3 with (R)-N-[(benzo[b]furan-2-ylmethoxy)-carbonyl-2-methyltryptophan 4 provided [R-(R* , S*)] {1-(1H-indole-3-ylmethyl)-1-methyl-2-oxo-2-[(1-[U-ring-14C]phenylethyl) amino]ethyl} carbamic acid benzo[b]furan-2-ylmethyl ester (CI-1021), a potential antiemetic agent.
Rh-Catalyzed N-O Bond Cleavage of Anthranil: A C-H Amination Reagent for Simultaneous Incorporation of Amine and a Functional Group
Zou, Miancheng,Liu, Jianzhong,Tang, Conghui,Jiao, Ning
, p. 3030 - 3033 (2016)
A novel Rh(III)-catalyzed C-H bond amination with the simultaneous release of a formyl group at distal positions is realized employing anthranil as a new type of C-H amination reagent. This chemistry provides an efficient protocol for the synthesis of 2-a
Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products
Zhang, Xiao,Rovis, Tomislav
supporting information, p. 21211 - 21217 (2021/12/27)
Oximes are valuable synthetic intermediates for the preparation of a variety of functional groups. To date, the stereoselective synthesis of oximes remains a major challenge, as most current synthetic methods either provide mixtures of E and Z isomers or furnish the thermodynamically preferred E isomer. Herein we report a mild and general method to achieve Z isomers of aryl oximes by photoisomerization of oximes via visible-light-mediated energy transfer (EnT) catalysis. Facile access to (Z)-oximes provides opportunities to achieve regio- and chemoselectivity complementary to those of widely used transformations employing oxime starting materials. We show an enhanced one-pot protocol for photocatalyzed oxime isomerization and subsequent Beckmann rearrangement that enables novel reactivity with alkyl groups migrating preferentially over aryl groups, reversing the regioselectivity of the traditional Beckmann reaction. Chemodivergent N- or O- cyclizations of alkenyl oximes are also demonstrated, leading to nitrones or cyclic oxime ethers, respectively.
Palladium-catalyzed C-H activation/C-C cross-coupling reactions: Via electrochemistry
Ma, Cong,Zhao, Chuan-Qi,Li, Yi-Qian,Zhang, Li-Pu,Xu, Xue-Tao,Zhang, Kun,Mei, Tian-Sheng
supporting information, p. 12189 - 12192 (2017/11/16)
Palladium-catalyzed C-H activation/C-C cross-coupling reactions typically require stoichiometric chemical oxidants and exogenous ligands. However, there are significant disadvantages associated with the use of traditional stoichiometric oxidants. To overcome these issues, we have developed an electrochemical strategy to achieve methylation and acylation.
