62214-39-5Relevant articles and documents
Enzymatic resolution of 1,1-dimethoxybut-3-en-2-ol and 1,1-dimethoxypent-4- en-2-ol, α-hydroxyaldehyde precursors for aldol-type reactions
Chenevert, Robert,Gravil, Sebastien,Bolte, Jean
, p. 2081 - 2086 (2005)
Hydroxyacetals 2 and 3 were resolved by acylation with vinyl acetate in the presence of lipases in organic media. The reverse reaction, the enzymatic hydrolysis of the corresponding acetates, was also highly stereoselective and provided the opposite enant
The preparation of enantiomerically pure 3,4-epoxy-1-butene and 3-butene-1,2-diol
Boaz, Neil W.,Falling, Stephen N.,Moore, Mary K.
, p. 1615 - 1617 (2005)
Single enantiomer 2-hydroxy-3-butenyl tosylate is a key precursor for single enantiomer 3,4-epoxy-1-butene and 3-butene-1,2-diol. The epoxide results from ring-closure of the hydroxytosylate while the diol is obtained through the intermediacy of the corresponding cyclic carbonate. This latter sequence avoids the loss of enantiomeric purity observed through direct hydrolysis. Georg Thieme Verlag Stuttgart.
The Role of Trichloroacetimidate to Enable Iridium-Catalyzed Regio- And Enantioselective Allylic Fluorination: A Combined Experimental and Computational Study
Sorlin, Alexandre M.,Mixdorf, Jason C.,Rotella, Madeline E.,Martin, Robert T.,Gutierrez, Osvaldo,Nguyen, Hien M.
supporting information, p. 14843 - 14852 (2019/10/11)
Asymmetric allylic fluorination has proven to be a robust and efficient methodology with potential applications for the development of pharmaceuticals and practical synthesis for 18F-radiolabeling. A combined computational (dispersion-corrected
Functionalizable Stereocontrolled Cyclopolyethers by Ring-Closing Metathesis as Natural Polymer Mimics
Alkattan, Mohammed,Prunet, Jo?lle,Shaver, Michael P.
supporting information, p. 12835 - 12839 (2018/09/25)
Whereas complex stereoregular cyclic architectures are commonplace in biomacromolecules, they remain rare in synthetic polymer chemistry, thus limiting the potential to develop synthetic mimics or advanced materials for biomedical applications. Herein we
Asymmetric Hydroformylation of 4-Vinyl-1,3-dioxolan-2-one
Pongrácz, Péter,Kollár, László
, p. 1430 - 1436 (2017/03/27)
A chiral cyclic carbonate, 4-vinyl-1,3-dioxolan-2-one was used as racemic substrate in asymmetric hydroformylation. The catalysts were formed in situ from “pre-formed” PtCl2(diphosphine) and tin(II) chloride. (2S,4S)-2,4-Bis(diphenylphosphinopentane ((S,S)-BDPP)), (S,S)-2,3-O-izopropylidine-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane ((S,S)-DIOP)), and (R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ((R)-BINAP)) were used as optically active diphosphine ligands. The platinum-containing catalytic systems provided surprisingly high activity. The hydroformylation selectivities of up to 97% were accompanied by perfect regioselectivity towards the dioxolane-based linear aldehyde. The enantiomeric composition of all components in the reaction mixture was determined and followed throughout the reaction. The unreacted 4-vinyl-1,3-dioxolan-2-one was recovered in optically active form. The kinetic resolution was rationalized using the enantiomeric composition of the substrate and the products.
Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid
Chatterjee, Bhaskar,Mondal, Dhananjoy,Bera, Smritilekha
, p. 1170 - 1185,16 (2020/09/09)
A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores.
Synthesis and stereospecificity of 4,5-disubstituted oxazolidinone ligands binding to T-box riboswitch RNA
Orac, Crina M.,Zhou, Shu,Means, John A.,Boehm, David,Bergmeier, Stephen C.,Hines, Jennifer V.
scheme or table, p. 6786 - 6795 (2011/12/04)
The enantiomers and the cis isomers of two previously studied 4,5-disubstituted oxazolidinones have been synthesized, and their binding to the T-box riboswitch antiterminator model RNA has been investigated in detail. Characterization of ligand affinities and binding site localization indicates that there is little stereospecific discrimination for binding antiterminator RNA alone. This binding similarity between enantiomers is likely due to surface binding, which accommodates ligand conformations that result in comparable ligand-antiterminator contacts. These results have significant implications for T-box antiterminator-targeted drug discovery and, in general, for targeting other medicinally relevant RNA that do not present deep binding pockets.
Three step synthesis of single diastereoisomers of the vicinal trifluoro motif
Brunet, Vincent A.,Slawin, Alexandra M. Z.,O'Hagan, David
supporting information; experimental part, (2010/04/22)
A three step route to single diastereoisomers of the vicinal trifluoromethyl motif is described. The route starts from either syn- or anti-α,β-epoxy alcohols and takes a direct approach in that each of the three steps introduces a fluorine atom in a regio- and stereospecific manner. Starting from either the syn- or the anti-α,β-epoxy alcohol, stereospecific reactions generate two separate diastereoisomeric series of this motif. The route is a significant improvement on an earlier six step strategy.
"Cassette" in situ enzymatic screening identifies complementary chiral scaffolds for hydrolytic kinetic resolution across a range of epoxides
Dey, Sangeeta,Powell, Douglas R.,Hu, Chunhua,Berkowitz, David B.
, p. 7010 - 7014 (2008/09/17)
(Figure Presented) Put the cassette in: An in situ enzymatic screen can give real-time estimates of the sense and magnitude of enantioselectivity across more than one substrate. Screening identified CoIII-salen catalysts with β-pinene- and α-naphthylalanine-derived chiral scaffolds with broad, yet complementary, substrate specificities. ADH = alcohol dehydrogenase, HL = horse liver, LK = Lactobacillus kefir, salen = (salicylidene) ethylenediamine.
Synthesis of the fully functionalized ABCDE ring moiety of ciguatoxin
Kobayashi, Shoji,Alizadeh, Babak H.,Sasaki, Shin-Ya,Oguri, Hiroki,Hirama, Masahiro
, p. 751 - 754 (2007/10/03)
A fully functionalized ABCDE ring moiety of ciguatoxin (CTX), the major causative agent of ciguatera poisoning, was synthesized for the first time. The present strategy involves the efficient installation of the C5-dihydroxybutenyl substituent and constru
