Enantioselective Synthesis of SM-130686 Based on the Development of Asymmetric Cu(I)F Catalysis To Access 2-Oxindoles Containing a Tetrasubstituted Carbon was written by Tomita, Daisuke;Yamatsugu, Kenzo;Kanai, Motomu;Shibasaki, Masakatsu. And the article was included in Journal of the American Chemical Society in 2009.Name: Chloromethyl benzoate This article mentions the following:
Two different catalytic enantioselective approaches to 3-aryl- and 3-alkenyl-3-hydroxy-2-oxindoles have been developed. First, enantioselective arylation and alkenylation reactions of isatins using aryltrimethoxysilanes and alkenyltrimethoxysilanes as nucleophiles can be catalyzed by a complex of CuF with structurally tuned Taniaphos in the presence of a catalytic amount of ZnF2. Despite the wide substrate scope, this intermol. reaction was not applicable to a catalytic enantioselective synthesis of SM-130686 (I·HCl), a highly potent, orally active growth hormone secretagogue containing a sterically congested chiral tetrasubstituted carbon. Therefore, an intramol. catalytic enantioselective arylation of α-keto amides was developed, taking advantage of the robustness of arylboronate reagents under multiple synthetic conversions and silica gel column chromatog. purification A complex of CuF with Ph-BPE (II) catalyzed the enantioselective arylation of α-keto amide III, affording product IV in 85% ee. The addition of ZnF2 to this intramol. reaction was not necessary. The first enantioselective synthesis of SM-130686 was achieved using this catalytic methodol. Because 2-oxyindoles are a versatile motif for biol. active compounds, the two types of Cu-catalyzed asym. reactions developed here will be useful for the synthesis of other natural products and pharmaceutical leads. In the experiment, the researchers used many compounds, for example, Chloromethyl benzoate (cas: 5335-05-7Name: Chloromethyl benzoate).
Chloromethyl benzoate (cas: 5335-05-7) belongs to organic chlorides. Chlorination modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than water due to the higher atomic weight of chlorine versus hydrogen. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.Name: Chloromethyl benzoate
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Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics