113260-57-4Relevant academic research and scientific papers
Regioselective Single-Electron Tsuji-Trost Reaction of Allylic Alcohols: A Photoredox/Nickel Dual Catalytic Approach
Wang, Zheng-Jun,Zheng, Shuai,Romero, Eugénie,Matsui, Jennifer K.,Molander, Gary A.
, p. 6543 - 6547 (2019)
A radical-mediated functionalization of allyl alcohol derived partners with a variety of alkyl 1,4-dihydropyridines via photoredox/nickel dual catalysis is described. This transformation transpires with high linear and E-selectivity, avoiding the requirement of harsh conditions (e.g., strong base, elevated temperature). Additionally, using aryl sulfinate salts as radical precursors, allyl sulfones can also be obtained. Kinetic isotope effect experiments implicated oxidative addition of the nickel catalyst to the allylic electrophile as the turnover-limiting step, supporting previous computational studies.
Efficient synthesis of functionalized olefins by Wittig reaction using Amberlite resin as a mild base
Valkute, Tushar R.,Aratikatla, Eswar K.,Bhattacharya, Asish K.
, p. 581 - 589 (2017/03/15)
A convenient procedure for the synthesis of olefins by the reaction of stabilized, semistabilized, and nonstabilized phosphorous ylides with various aldehydes or ketone using Amberlite resin as a mild base is described. Our developed method offers facile and racemization-free synthesis of α,β-unsaturated amino esters and chiral allylic amine. The developed methodology offers mild reaction conditions, high efficiency, and facile isolation of the final products, a practical alternative to known procedures.
Alkyl transfer from C-C cleavage: Replacing the nitro group of nitro-olefins
Li, Guangxun,Wu, Lei,Lv, Gang,Liu, Hongxin,Fu, Qingquan,Zhang, Xiaomei,Tang, Zhuo
, p. 6246 - 6248 (2014/06/09)
Alkyl substituted Hantzsch esters are rationally used as alkylation reagents to replace the nitro groups of nitro olefins to give excellent yields of trans-olefins. The reaction mechanism is considered to proceed through a free radical mechanism, which is different from the corresponding transfer alkylation of imines. This journal is the Partner Organisations 2014.
Tandem copper-catalyzed enantioselective allylation-metathesis
Alexakis, Alexandre,Croset, Karine
, p. 4147 - 4149 (2007/10/03)
(matrix presented) Grignard reagents undergo enantioselective (up to 86% ee) copper-catalyzed SN2′ substitution on achiral allylic chlorides. The reaction is wide in scope for both the Grignard reagent and the allylic substrate. The resulting terminal alkene could be submitted to intra-or intermolecular metathesis to afford new chiral synthons. The experimental conditions are compatible with a one-pot overall substitution - metathesis procedure without loss of enantioselectivity.
Protonation and Alkykation of 1-Arylpropenyl-lithium
Tanaka, Jiro,Nojima, Masatomo,Kusabayashi, Shigekazu,Nagase, Shigeru
, p. 673 - 678 (2007/10/02)
The protonation and alkylation of 1-arylpropenyl-lithium (1a-c) in ether was undertaken systematically; the regio- and stereo-chemistry being influenced by various factors.The characteristic features are as follows. (a) Protonation occurs predominantly at C-3, whereas the sterically more crowded C-1 is the more favoured site for alkylation, and (b) although 1-arylpropenyl-lithium (1) seems to exist mainly as the E-isomer, in some cases the product (3) or (5) having the Z-configuration is produced from attack at C-3 in a significant amount together with the E-isomer, e.g. protonation by oxygen acids in the presence or absence of tetramethylethylenediamine and methylation of the p-methoxy derivative (1a).
