Computed Properties of C7H13BrO2. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Gold-catalysed asymmetric net addition of unactivated propargylic C-H bonds to tethered aldehydes. Author is Li, Ting; Cheng, Xinpeng; Qian, Pengcheng; Zhang, Liming.
The asym. one-step net addition of unactivated propargylic C-H bonds to aldehydes such as 7-(dimethyl(phenyl)silyl)hept-6-ynal, 4-(benzyloxy)-7-(tert-butyldimethylsilyl)hept-6-ynal, 7-(tert-Butyldimethylsilyl)-2-phenylhept-6-ynal, etc. leads to an atom-economic construction of versatile chiral homopropargylic alcs. e.g., I, but has not yet been realized. Here, implementation in an intramol. manner under mild reaction conditions have been showed. This chem.-via cooperative gold catalysis enabled by chiral bifunctional phosphine ligands (1R/1S)-II (R = Me, Cy; R1 = H, Me)-achieves asym. catalytic deprotonation of propargylic C-H (pKa > 30) by a tertiary amine group (pKa ≈ 10) of the ligand in the presence of much more acidic aldehydic α-hydrogens (pKa ≈ 17). The reaction exhibits a broad scope and readily accommodates various functional groups. The cyclopentane/cyclohexane-fused homopropargylic alc. products e.g., III are formed with excellent enantiomeric excesses and high trans-selectivities with or without a preexisting substrate chiral center. D. functional theory studies of the reaction support the conceived reaction mechanism and the calculated energetics corroborate the observed stereoselectivity and confirm addnl. metal-ligand cooperation.
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