110598-66-8Relevant academic research and scientific papers
Degradation of aldehydes to one carbon lower homologs
Belotti, Damien,Andreatta, Ga?lle,Pradaux, Fabienne,BouzBouz, Samir,Cossy, Janine
, p. 3613 - 3615 (2003)
Degradation of aldehydes to one carbon lower homologs has been achieved by using a mixture of N-methylmorpholine, N-methylmorpholine N-oxide, a catalytic amount of OsO4 and NaIO4 in a mixture of acetone/H2O.
The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia–Kocienski reaction
Rehman, Mintu,Surendran, Sravya,Siddavatam, Nagendra,Rajendar, Goreti
supporting information, p. 329 - 333 (2022/01/20)
Modified reaction conditions for improved E-selectivity of olefins in the Julia–Kocienski reaction of aldehydes having α-coordinating substituents are demonstrated. The chelating groups in aldehydes are expected to stabilize the syn-transition state with metal ions, whereas the weakly coordinating quaternary ammonium ions are devoid of all possible chelating interactions to enhance E-selectivity. A systematic investigation is presented to study the size of the neighbouring protecting groups of aldehydes and their chelation effect on E/Z-selectivity in the Julia–Kocienski reaction.
Kinetic Resolution of Racemic Aldehydes through Asymmetric Allenoate γ-Addition: Synthesis of (+)-Xylogiblactone A
Park, Saehansaem,Pak, Gyungah,Oh, Changhwa,Lee, Jieun,Kim, Jimin,Yu, Chan-Mo
supporting information, p. 7660 - 7664 (2019/10/02)
A synthesis of (+)-xylogiblactone A has been achieved from t-butyl 2-methylbuta-2,3-dienoate in a linear three-step sequence. The key elements of the synthesis include a kinetic resolution of racemic 2-silyoxyaldehyde through the allenoate γ-addition to y
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
supporting information, p. 1150 - 1159 (2019/01/11)
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.
Preparation of enol ester epoxides and their ring-opening to α-silyloxyaldehydes
Friestad, Gregory K.,Sreenilayam, Gopeekrishnan,Cannistra, Joseph C.,Slominski, Luke M.
experimental part, p. 5064 - 5067 (2012/09/25)
The Z-selective ruthenium-catalyzed addition of aromatic carboxylic acids to alkynes was followed by dioxirane epoxidation to furnish enol ester epoxides with cis configuration. Upon treatment of enol ester epoxides with tert-butyldimethylsilyl triflate i
Improved conditions for the Kiliani-Fischer synthesis
Adje,Vogeleisen,Uguen
, p. 5893 - 5896 (2007/10/03)
DIBA-H reduction of O-TBDMS derivatives of cyanohydrins, followed by hydrolysis with a pH4 tartaric-buffer at low temperature produces the corresponding O-protected 2-hydroxy aldehydes in very high yields.
