58059-08-8Relevant articles and documents
ION PAIR CATALYSIS OF TUNGSTATE AND MOLYBDATE
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Page/Page column 42-43; 69-75, (2017/10/30)
D The present invention relates to ion pair catalysts (I) comprising the cationic bisguanidinium ligand (A) and diperoxomolybdate anion (B). The present invention also relates to ion pair catalysts (III) comprising the cationic bisguanidinium ligand (C) and peroxotungstate anion (D). It further relates to the use of the said catalysts in the manufacture of enantiomerically enriched sulfoxides.
Stereocontrol by quaternary centres: A stereoselective synthesis of (-)-luminacin D
Bartlett, Nathan,Gross, Leona,Peron, Florent,Asby, Daniel J.,Selby, Matthew D.,Tavassoli, Ali,Linclau, Bruno
supporting information, p. 3306 - 3310 (2014/04/03)
Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating α-ether substituent, even if the α-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin D.
Diastereofacial selectivity in aldol-type condensation induced by optically pure α-sulfinyl acetate with α-substituted aldehydes
Bauder, Claude
, p. 2243 - 2246 (2008/09/19)
Highly diastereoselective aldol-type condensations induced by the chiral magnesium enolate of tert-butyl p-tolyl sulfinyl acetate were performed with optically pure alkyl or hydroxy α-substituted aldehydes. The addition of chiral α-sulfinyl acetate to var
3. Naphthopyranquinone Antibiotics: Novel Enantioselective Syntheses of Frenolicin B and Some of Its Stereoisomers
Masquelin, Thierry,Hengartner, Urs,Streith, Jacques
, p. 43 - 58 (2007/10/03)
Two new enantioselective syntheses of the naphthopyranquinone antibiotic frenolicin B (1), of its enantiomer 2, and of its diastereoisomers 3 and 4 were accomplished using two different routes from optically active β-hydroxy esters (R)- and (S)-11 and 18.
Asymmetric synthesis of chiral sulfoxides and sulfinimines by using N-sulfinylsultam
Oppolzer, Wolfgang,Froelich, Olivier,Wiaux-Zamar, Chantal,Bernardinelli, Gerald
, p. 2825 - 2828 (2007/10/03)
Bornane-10,2-sultam 1 is stereoselectively converted by DMAP-assisted sulfinylation to diastereomerically pure (2R)-N-[(R)-p-tolylsulfinyl]-bornane-10,2-sultam 2 in 77% yield. The crystalline sulfinylating agent 2 reacts with a variety of nucleophiles to afford sulfoxides 3 and sulfinimines 5 in excellent yields and enantioselectivities.
Asymmetric synthesis of 4-phenyl-1,5-diazacyclooctan-2-one using optically active vinyl sulfoxides
Itoh,Matsuyama,Yoshida,Kamigata,Iyoda
, p. 3121 - 3130 (2007/10/03)
Both enantiomers of (S)- and (R)-4-phenyl-1,5-diazacyclooctan-2-ones (7) were synthesized stereoselectively with good optical purity by the asymmetric conjugate addition of pyrazolidine to optically active vinyl sulfoxides, t-butyl (E)-2-[(R)- and (S)-p-tolylsulfinyl]cinnamates, respectively. Starting from 7, a synthesis of optically active homaline was achieved.
Oxidation of methyl p-tolyl sulfide with backers' yeast: preparation of a synthon of the mevinic acid-type hypocholestemic agents
Beecher, Jean,Brackenridge, Ian,Roberts, Stanley M.,Tang, Jenny,Willetts, Andrew J.
, p. 1641 - 1644 (2007/10/02)
Bakers' yeast oxidized methyl p-tolyl sulfide to produce the R-sulfoxide 1 in good yield and high enantiomeric excess; the sulfoxide 1 was used to prepare (4R,6S)-tert-butyldimethylsilyloxy-6-hydroxymethyltetrahydropyran-2-one 15.
Asymmetric synthesis of chiral organosulfur compounds using N-sulfinyloxazolidinones
Evans, David A.,Faul, Margaret M.,Colombo, Lino,Bisaha, John J.,Clardy, Jon,Cherry, David
, p. 5977 - 5985 (2007/10/02)
This paper describes a new class of chiral sulfinyl transfer reagents, 4 and 5 (R = aryl, alkyl), which are readily prepared from the oxazolidinones derived from (4R,5S)-norephedrine (HXN) and (4S)-phenylalanine (HXp), respectively. These N-suIfinyloxazolidinone reagents can be synthesized either by sulfinylation-of the metalated oxazolidinones or by oxidation of the derived N-sulfenimides to afford the diastereomeric N-sulfinyloxazolidinones which may be readily purified by chromatography. These sulfinylating agents react with a wide range of nucleophiles such as Grignard reagents, enolates, lithium alkoxides, or metalated amides, with inversion of configuration at the sulfur center to afford the derived chiral sulfoxides, sulfinate esters, and sulfinamides in high yields and enantioselectivities. Competition experiments have established that this family of chiral sulfinylating agents is at least 100 times as reactive as the corresponding menthyl sulfinate esters toward Grignard reagents.
Asymmetric Periodate Oxidation of Functionalized Sulfides Catalyzed by Bovine Serum Albumin
Colonna, Stefano,Banfi, Stefano,Fontana, Francesca,Sommaruga, Maurizio
, p. 769 - 771 (2007/10/02)
The asymmetric oxidation of the functionalized sulfides with sodium metaperiodate in the presence of a catalytic amount of bovine serum albumin (BSA) affords the corresponding sulfoxides with enantiomeric excess (ee) up to 69.3percent.The influence of the
SYNTHESES ASYMETRIQUES DE β-HYDROXYACIDES PAR CONDENSATION D'ANIONS ENOLATES D'ESTERS α-SULFINYLE CHIRAUX SUR DES COMPOSES CARBONYLES
Mioskowski, Charles,Solladie, Guy
, p. 227 - 236 (2007/10/02)
A stereospecific synthesis of (R)-(+)-t-butyl p-tolylsulfinyl acetate 2 is described.The aldol-type condensation of this reagent leads to β-hydroxyacids in good chemical and optical yields.The determination of the absolute configuration of the condensatio