159506-59-9Relevant academic research and scientific papers
Kinetic Resolution of Allylic Alcohol with Chiral BINOL-Based Alkoxides: A Combination of Experimental and Theoretical Studies
Liu, Yidong,Liu, Song,Li, Dongmei,Zhang, Nan,Peng, Lei,Ao, Jun,Song, Choong Eui,Lan, Yu,Yan, Hailong
, p. 1150 - 1159 (2019)
The development and characterization of enantioselective catalytic kinetic resolution of allylic alcohols through asymmetric isomerization with chiral BINOL derivatives-based alkoxides as bifunctional Br?nsted base catalysts were described in the study. A number of chiral BINOL derivatives-based alkoxides were synthesized, and their structure-enantioselectivity correlation study in asymmetric isomerization identified a promising chiral Br?nsted base catalyst, which afforded various chiral secondary allylic alcohols (ee up to 99%, S factor up to >200). In the mechanistic study, alkoxide species were identified as active species and the phenol group of BINOL largely affected the high reactivity and enantioselectivity via hydrogen bonding between the chiral Br?nsted base catalyst and substrates. The strategy is the first successful synthesis strategy of various chiral secondary allylic alcohols through enantioselective transition-metal-free base-catalyzed isomerization. The applicability of the strategy had been demonstrated by the synthesis of the bioactive natural product (+)-veraguensin.
Concave Reagents, 15. New Concave 1,10-Phenanthrolines: Catalysts for the Alcohol Addition to Ketenes and Ligands in Transition Metal Complexes
Luening, Ulrich,Mueller, Michael,Gelbert, Markus,Peters, Karl,Schnering, Hans Georg von,Keller, Manfred
, p. 2297 - 2306 (2007/10/02)
By bridging tetrahydroxy-1,10-phenanthrolines 9 by ditosylates 10 or diiodides 11 concave 1,10-phenanthrolines 1 were synthesized.Their concave shape was proven by X-ray analyses of 1a and 1c, their basicities were determined by photometric titrations.Compounds 1a-g are active in the base-catalyzed addition of alcohols to ketenes and form stable metal ion complexes with transition metal salts. - Key Words: Macrocycles / Broensted plot / Catalysis, base / Basicity / Transition metal complexes
