2612-30-8Relevant articles and documents
NaBH4-InCl3-mediated one-pot chemo- and stereoselective decarboxylative reduction of α-aza gem-dicarboxylic esters to monoalcohols
Haldar, Pranab,Ray, Jayanta K.
, p. 4341 - 4343 (2005)
(Chemical Equation Presented) The combination of NaBH4 and a catalytic amount of InCl3 provides a one-pot method for chemo- and stereoselective decarboxylative reduction of gem-dicarboxylic esters 1 to monoalcohols 2 in the presence
MODULATORS OF HSD17B13 AND METHODS OF USE THEREOF
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Paragraph 0436, (2021/01/23)
The disclosure relates to compounds and pharmaceutical compositions capable of modulating the hydroxysteroid 17-beta dehydrogenase (HSD17B) family member proteins including inhibiting the HSD17B member proteins, e.g. HSD17B13. The disclosure further relates to methods of treating liver diseases, disorders, or conditions with the compounds and pharmaceutical compositions disclosed herein, in which the HSD17B family member protein plays a role.
A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Br?nsted- And Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings
Strassfeld, Daniel A.,Algera, Russell F.,Wickens, Zachary K.,Jacobsen, Eric N.
supporting information, p. 9585 - 9594 (2021/07/19)
Generality in asymmetric catalysis can be manifested in dramatic and valuable ways, such as high enantioselectivity across a wide assortment of substrates in a given reaction (broad substrate scope) or as applicability of a given chiral framework across a variety of mechanistically distinct reactions (privileged catalysts). Reactions and catalysts that display such generality hold special utility, because they can be applied broadly and sometimes even predictably in new applications. Despite the great value of such systems, the factors that underlie generality are not well understood. Here, we report a detailed investigation of an asymmetric hydrogen-bond-donor catalyzed oxetane opening with TMSBr that is shown to possess unexpected mechanistic generality. Careful analysis of the role of adventitious protic impurities revealed the participation of competing pathways involving addition of either TMSBr or HBr in the enantiodetermining, ring-opening event. The optimal catalyst induces high enantioselectivity in both pathways, thereby achieving precise stereocontrol in fundamentally different mechanisms under the same conditions and with the same chiral framework. The basis for that generality is analyzed using a combination of experimental and computational methods, which indicate that proximally localized catalyst components cooperatively stabilize and precisely orient dipolar enantiodetermining transition states in both pathways. Generality across different mechanisms is rarely considered in catalyst discovery efforts, but we suggest that it may play a role in the identification of so-called privileged catalysts.
