25705-34-4Relevant articles and documents
Enantioselective synthesis of the strigolactone mimic (+)-GR24
Bromhead, Liam J.,Visser, Johan,McErlean, Christopher S. P.
, p. 1516 - 1520 (2014)
A short and cost-effective synthesis of the important strigolactone analogue (+)-GR24 is described. Central to this new approach is the concise, enantioselective synthesis of the A-C ring system.
Enhanced enantioselectivity in heterogeneous manganese-catalyzed asymmetric epoxidation with nanosheets modified amino acid Schiff bases as ligands by modulating the orientation and the arrangement order
An, Zhe,Han, Hongbo,He, Jing,Jiang, Yitao,Ping, Qi,Shu, Xin,Song, Hongyan,Tang, Yuanzhong,Wang, Wenlong,Xiang, Xu,Zhu, Yanru
, p. 22 - 36 (2021/08/25)
Catalytic enantioselective epoxidation of olefins plays an important role in the production of optically-active epoxy. Transition-metal complexes prove efficient for the catalytic epoxidation of un-functionalized olefins by employing privileged chiral lig
Pseudophedrine-Derived Myers Enolates: Structures and Influence of Lithium Chloride on Reactivity and Mechanism
Zhou, Yuhui,Jermaks, Janis,Keresztes, Ivan,MacMillan, Samantha N.,Collum, David B.
supporting information, p. 5444 - 5460 (2019/03/29)
The structures and reactivities of pseudoephedrine-derived dianionic Myers enolates are examined. A combination of NMR and IR spectroscopic, crystallographic, and computational data reveal that the homoaggregated dianions form octalithiated tetramers displaying S4-symmetric Li8O8 cores and overall C2 symmetry. Computational and isotopic labeling studies reveal strong N-Li contacts in the carboxamide enolate moiety. The method of continuous variations proves deceptive, as octalithiated tetrameric homoaggregates afford hexalithiated trimeric heteroaggregates. A lithium diisopropylamide-lithium enolate mixed aggregate is found to be a C2-symmetric hexalithiated species incorporating two enolate dianions and two lithium diisopropylamide (LDA) subunits. Structural and rate studies show that lithium chloride has little effect on the dynamics of the enolate homoaggregates but forms adducts of unknown structure. Rate studies of alkylations indicate that the aging of the aggregates can have effects spanning orders of magnitude. The LiCl-enolate adduct dramatically accelerates the reaction but requires superstoichiometric quantities owing to putative autoinhibition. Efforts and progress toward eliminating the requisite large excess of LiCl are discussed.
Copper Catalyzed One-Pot Three-Component Imination-Alkynylation-aza-Michael Sequence: Enantio- And Diastereoselective Syntheses of 1,3-Disubstituted Isoindolines and Tetrahydroisoquinolines
Das, Braja Gopal,Shah, Sadhna,Singh, Vinod K.
supporting information, p. 4981 - 4985 (2019/07/08)
An enantio- and diastereoselective syntheses of 1, 3-disubstituted isoindolines and tetrahydroisoquinolines via CuI-Pybox-diPh catalyzed one-pot imination-alkynylation-aza-Michael sequence has been reported. The three-component reaction produces one C-C and two C-N bonds sequentially with high yield (up to 92%), enantioselectivity (up to 99%), and diastereoselectivity (up to 9:1) in a single operation. Furthermore, the synthetic utility of the product has been demonstrated by LiAlH4 reduction of ester and hydrogenation of alkyne functionality without losing the stereoselectivity.