- Disulfide-based metal-free α-sulfanylation of ketones
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An eco-friendly methodology for the direct α-sulfanylation of ketones, has been developed. The procedure, based on the use of functionalized diaryldisulfides and catalyzed by d,l-proline, represents a mild and efficient approach for the preparation of α-arylthio-ketones.
- Vaquer, Andrea F.,Frongia, Angelo,Secci, Francesco,Tuveri, Enrica
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p. 96695 - 96704
(2015/11/24)
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- The MARDi cascade: A Michael-initiated domino-multicomponent approach for the stereoselective synthesis of seven-membered rings
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The MARDi cascade is a recently invented three-component Michael-initiated condensation involving 1,3-dicarbonyl derivatives. It allows regio- and stereocontrolled access to a variety of functionalised and substituted seven-membered rings. The substitutio
- Coquerel, Yoann,Filippini, Marie-Helene,Bensa, David,Rodriguez, Jean
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scheme or table
p. 3078 - 3092
(2009/04/11)
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- Facile and efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions
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A novel sulfenylation method induced by aromatization of quinone mono-O,S-acetals is described. These sulfenylation reagents readily react with silyl enolethers or electron rich aromatic compounds to give sulfenylation products under mild conditions. In particular, O,S-acetal 2j, which possesses a pentafluorophenylthio function, is the most effective reagent from the standpoint of the adaptability for various substrates.
- Matsugi,Murata,Gotanda,Nambu,Anilkumar,Matsumoto,Kita
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p. 2434 - 2441
(2007/10/03)
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- A new sulfenylation reagent, 3-phenylsulfenyl-2-(N- cyanoimino)thiazolidine, and its optically active version
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We have developed a new sulfenylation reagent, 3-phenylsulfenyl-2-(N- cyanoimino)thiazolidine 3, that is readily available and stable upon storage. Compound 3 easily reacts with amines or thiols to give the corresponding sulfenamides or asymmetrical disulfides in excellent yields. It was also found that the α-sulfenylation reaction of carbonyl compounds with 3 proceeds smoothly. Furthermore, optically active 4-diphenylmethyl derivative 4 was synthesized as an asymmetric sulfenylation reagent, which realized 96% e.e. upon α-sulfenylation of a cyclic β-keto ester.
- Tanaka,Azuma,Fang,Uchida,Iwata,Ishida,In,Maezaki
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- A novel efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions
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A novel method for sulfenylation induced by aromatization of quinone mono-O,S-acetals is described.
- Matsugi, Masato,Gotanda, Kentoku,Murata, Kenji,Kita, Yasuyuki
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p. 1387 - 1388
(2007/10/03)
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- New Mild Methodology for the Synthesis of α-Phenylthio and α-Phenylseleno Ketones
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Treatment of trimethylsilyl enol ethers with the adduct 1, derived from chloramine-T and (PhS)2, gave good yields of α-phenylthioketones.The selenium version of this reagent 2 gave α-phenylselenoketones.
- Magnus, Philip,Rigollier, Pascal
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p. 6111 - 6114
(2007/10/02)
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- Diastereoselective Sulfenylation Reactions Employing N-(Phenylthio)lactams under Nonbasic Conditions
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Silyl enol ethers and silyl ketene acetals react with sulfenamides in the presence of trimethylsilyl triflate to give the corresponding trans-sulfenylated ketones and lactones.
- Wilson, Lawrence J.,Liotta, Dennis C.
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p. 1948 - 1950
(2007/10/02)
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- CHEMISTRY OF α-NITROEPOXIDES: SYNTHESIS OF USEFUL INTERMEDIATES VIA NUCLEOPHILIC RING OPENING OF α-NITROEPOXIDES
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Various α-nitroepoxides are converted into corresponding 1,2-diketones via two different ways of ring opening viz. with Pd(O) and with DMSO/BF3*EtO2 (or ClSiMe3).In addition to this, a variety of nucleophiles are reacted with α-nitrocyclopentene oxide 6 and α-nitrocyclohexene oxide 7 to form the corresponding α-substituted ketones which are useful intermediates in organic synthesis.Two of the products so obtained viz. 32 and 33 are also transformed further into optically active thialactones 38 and 39 respectively via baker's yeast reduction followed by lactonisation.
- Vankar, Yashwant D.,Shah, Kavita,Bawa, Anita,Singh, Surendra P.
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p. 8883 - 8906
(2007/10/02)
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- Synthesis of Cyclic Allylic Sulphides (Ring Sizes 5-15) via Phenylthio Participation
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Dehydration of β-phenylthio alcohols occurs with PhS participation unless stereochemistry prevents it.Without PhS participation, mixtures of allylic and vinylic sulphides are formed, but with PhS participation routes to three families of cyclic allylic su
- Hannaby, Malcolm,Warren, Stuart
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p. 303 - 311
(2007/10/02)
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- CARBENOID TYPE BASE INDUCED RING EXPANSION OF THE ADDUCTS OF CYCLIC KETONES WITH BIS(PHENYLTHIO)METHYLLITHIUM
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In another application of the principle that metallo derivatives of bis(phenylthio)acetals behave as carbenoids when present in the same molecule with another anionic group, the adducts of cyclic ketones with bis(phenylthio)methyllithium react with an alk
- Abraham, William D.,Bhupathy, M.,Cohen, Theodore
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p. 2203 - 2206
(2007/10/02)
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- REARRANGEMENT OF CYCLIC ALCOHOLS WITH AN ADJACENT PHENYLTHIO (PhS-) GROUP: MIGRATION OF A PhS GROUP AROUND A RING.
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PhS migratoin around rings (size 5-15) gives allyl sulphides with a regioselectivity wich varies with ring size.
- Hannaby, Malcolm,Warren, Stuart
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p. 765 - 768
(2007/10/02)
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- A Cyclopentanone Annulation via Intramolecular Acylation of Alkylsilanes
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A facile construction of cyclopentanones is achieved via ring closure of 5-(trimethylsilyl)alkanoyl chlorides under the influence of AlCl3.
- Urabe, Hirokazu,Kuwajima, Isao
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p. 1140 - 1141
(2007/10/02)
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- IODOMETHYL PHENYL SULFOXIDE: REACTIVITY AND SYNTHETIC APPLICATIONS
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Lithio iodomethyl phenyl sulfoxides reacted with alkyl halides and carbonyl compounds to give adducts in good to moderate yields.Solvolysis of the carbonyl adducts led to sulfones or the ring expanded product.
- Reutrakul, Vichai,Panyachotipun, Chitchanun,Hahnvajanawong, Viwat,Sotheeswaran, S.
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p. 1825 - 1828
(2007/10/02)
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- REGIOSPECIFIC SYNTHESIS OF α-(PHENYLTHIO)KETONES VIA RHODIUM(II) ACETATE CATALYSED ADDITION OF THIOPHENOL TO α-DIAZOKETONES
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αα-Addition of thiophenol to α-diazoketones is catalysed efficiently by rhodium(II) acetate in benzene solution at room temperature, offering a convenient regiospecific route to a variety of α-(phenylthio)ketones.
- McKervey, M. Anthony,Ratananukul, Piniti
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p. 2509 - 2512
(2007/10/02)
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