《Hydrazide-Catalyzed Polyene Cyclization: Asymmetric Organocatalytic Synthesis of cis-Decalins》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Plamondon, Samuel J.; Warnica, Josephine M.; Kaldre, Dainis; Gleason, James L.. Quality Control of (3-Methoxy-2-methylphenyl)methanol The article mentions the following:
Polyene cyclizations offer rapid entry into terpenoid ring systems. Although enantioselective cyclizations of (E)-polyenes to form trans-decalin ring systems are well precedented, highly enantioselective cyclizations of (Z)-polyenes to form the corresponding cis-decalins have not been reported. Here, we describe the first application of iminium catalysis to the initiation of polyene cyclizations. Et 1,2-diazepane-1-carboxylate catalyzes the cyclization of polyenes bearing enal initiators. Moreover, chiral bicyclic hydrazides catalyze the cyclizations of (Z)-polyene substrates to form cis-decalins with enantioselectivities of up to 97:3 er. DFT calculations suggest the catalysts promote the reaction by stabilizing pos. charge as it develops during the bicyclization.(3-Methoxy-2-methylphenyl)methanol(cas: 33797-34-1Quality Control of (3-Methoxy-2-methylphenyl)methanol) was used in this study.
(3-Methoxy-2-methylphenyl)methanol(cas: 33797-34-1) belongs to ethers.Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. Quality Control of (3-Methoxy-2-methylphenyl)methanol They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however.
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem