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A new approach to the reduction of sulfoxides to sulfides with 1,3-dithiane in the presence of electrophilic bromine as catalyst.

The Journal of organic chemistry

Iranpoor N, Firouzabadi H, Shaterian HR.
PMID: 11975533
J Org Chem. 2002 May 03;67(9):2826-30. doi: 10.1021/jo016027y.

A new, mild, and novel method is described for the efficient deoxygenation of sulfoxides to their corresponding sulfides with 1,3-dithiane at room temperature in the presence of catalytic amounts of N-bromosuccinimide (NBS), 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO), or Br(2) as the source...

Nucleosides and Nucleotides. 151. Conversion of (Z)-2'-(Cyanomethylene)-2'-deoxyuridines into Their (E)-Isomers via Addition of Thiophenol to the Cyanomethylene Moiety Followed by Oxidative Syn-elimination Reactions(1).

The Journal of organic chemistry

Hassan AE, Nishizono N, Minakawa N, Shuto S, Matsuda A.
PMID: 11667465
J Org Chem. 1996 Sep 06;61(18):6261-6267. doi: 10.1021/jo960577s.

The Wittig reaction of 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-beta-D-erythro-pentofuranos-2-ulosyl]uracil (6) with Ph(3)P=CHCN afforded (Z)-2'-cyanomethylene derivative 7 exclusively. The (E)-isomer was accessed from its (Z)-isomer through a sequence of addition of thiophenol to the 2'-cyanomethylene moiety of the (Z)-isomer from the alpha-face, selectively, and...

Geometrically selective synthesis of functionalized beta,beta-disubstituted vinylic sulfoxides by Cu-catalyzed conjugate addition of organozinc reagents to 1-alkynyl sulfoxides.

Organic letters

Maezaki N, Sawamoto H, Yoshigami R, Suzuki T, Tanaka T.
PMID: 12688755
Org Lett. 2003 Apr 17;5(8):1345-7. doi: 10.1021/ol034289b.

[reaction: see text] A new synthetic method of chiral beta,beta-disubstituted vinylic sulfoxides bearing various functionalities has been developed by employing Cu-catalyzed conjugate addition of an organozinc reagent to chiral 1-alkynyl sulfoxide. Since the reaction proceeds with very high syn-selectivity,...

Prevalence of the alkyl/phenyl-folded conformation in benzylic compounds C6H5CH2-X-R (X=O, CH2, CO, S, SO, SO2): significance of the CH/pi interaction as evidenced by high-level ab initio MO calculations.

Chemistry (Weinheim an der Bergstrasse, Germany)

Takahashi O, Kohno Y, Saito K, Nishio M.
PMID: 12569468
Chemistry. 2003 Feb 03;9(3):756-62. doi: 10.1002/chem.200390084.

Ab initio MO calculations were carried out to examine the conformational energies of various benzylic compounds C(6)H(5)CH(2)XR (X=O, CH(2), CO, S, SO, SO(2); R=CH(3), C(2)H(5), iC(3)H(7), tC(4)H(9)) at the MP2/6-311G(d,p)//MP2/6-31G(d) level. Rotamers with R/Ph in gauche relationship are generally...

Methyloxorhenium(V) complexes with two bidentate ligands: syntheses and reactivity studies.

Inorganic chemistry

Shan X, Ellern A, Espenson JH.
PMID: 12495355
Inorg Chem. 2002 Dec 30;41(26):7136-42. doi: 10.1021/ic025952f.

Four new methyloxorhenium(V) complexes were synthesized: MeReO(PA)(2) (1), MeReO(HQ)(2) (2), MeReO(MQ)(2) (3), and MeReO(diphenylphosphinobenzoate)(2) (4) (in which PAH = 2-picolinic acid, HQH = 8-hydroxyquinoline, and MQH = 8-mercaptoquinoline). Although only one geometric structure has been identified crystallographically for 1,...

Enantioselective Carbon-Carbon Bond Formation via S(N)2' Displacements of Acyclic Allylic Mesylates(1).

The Journal of organic chemistry

Marino JP, Viso A, Lee JD, Fernández De La Pradilla R, Fernández P, Rubio MB.
PMID: 11671459
J Org Chem. 1997 Feb 07;62(3):645-653. doi: 10.1021/jo961292i.

The copper-mediated S(N)2' displacement of enantiomerically pure allylic mesyloxy vinyl sulfoxides takes place with high yields and stereoselectivities. In these adducts, the newly created chiral center is adjacent to a vinyl sulfoxide functionality which should allow for subsequent chirality...

Palladium(0)-Catalyzed Heteroarylation of 2- and 3-Indolylzinc Derivatives. An Efficient General Method for the Preparation of (2-Pyridyl)indoles and Their Application to Indole Alkaloid Synthesis.

The Journal of organic chemistry

Amat M, Hadida S, Pshenichnyi G, Bosch J.
PMID: 11671699
J Org Chem. 1997 May 16;62(10):3158-3175. doi: 10.1021/jo962169u.

Palladium(0)-catalyzed coupling of (1-(benzenesulfonyl)-2-indolyl)zinc chloride (1) and (1-(tert-butyldimethylsilyl)-3-indolyl)zinc chloride (6) with diversely substituted (alkyl, methoxy, methoxycarbonyl, nitro, hydroxy) 2-halopyridines gives the corresponding 2- and 3-(2-pyridyl)indoles [4 and 7 (or 8), respectively] in excellent yields. A series of other 3-(heteroaryl)indoles...

Asymmetric Synthesis with the Enzyme Coprinus Peroxidase: Kinetic Resolution of Chiral Hydroperoxides and Enantioselective Sulfoxidation.

The Journal of organic chemistry

Adam W, Mock-Knoblauch C, Saha-Möller CR.
PMID: 11674558
J Org Chem. 1999 Jun 25;64(13):4834-4839. doi: 10.1021/jo990201p.

The enzyme Coprinus peroxidase (CiP) was employed for the kinetic resolution of racemic hydroperoxides 1 and the asymmetric sulfoxidation of prochiral sulfides 4. Eleven hydroperoxides 1a-k were reduced by CiP and guaiacol as reductant under conditions of kinetic resolution...

Oxidation of Thioether Ligands in Pseudotetrahedral Cyclopentadienylruthenium Complexes: Toward a New Stereoselective Synthesis of Chiral Sulfoxides(1).

Inorganic chemistry

Schenk WA, Frisch J, Dürr M, Burzlaff N, Stalke D, Fleischer R, Adam W, Prechtl F, Smerz AK.
PMID: 11669873
Inorg Chem. 1997 May 21;36(11):2372-2378. doi: 10.1021/ic961280f.

Ionic ruthenium thioether complexes [Cp(LL')Ru(SRR')]PF(6) (LL' = Ph(2)PCH(2)PPh(2) (1), Ph(2)PC(2)H(4)PPh(2) (2), (Ph(3)P, CO) (3), Me(2)PC(2)H(4)PPh(2) (4), (S,S)-Ph(2)PCHMeCHMePPh(2) (5), SRR' = MeSPh (a), MeS-i-Pr (b), MeSBz (c), i-PrSBz (d), EtSBz (e), MeSCy (f), SC(4)H(8) (g)) were synthesized from the corresponding...

Oxidation of Sulfides to Sulfoxides with Hypervalent (tert-Butylperoxy)iodanes.

The Journal of organic chemistry

Ochiai M, Nakanishi A, Ito T.
PMID: 11671744
J Org Chem. 1997 Jun 27;62(13):4253-4259. doi: 10.1021/jo970081q.

Oxidation of sulfides with the crystalline (alkylperoxy)iodanes, 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-ones 2a and 2b, in acetonitrile-water or in dichloromethane, affords sulfoxides in high yields. Measurement of the relative rates of oxidation for a series of ring-substituted thioanisoles 3b (p-MeO), 3c (p-Me), and...

Asymmetric Sulfoxidation Catalyzed by a Vanadium-Containing Bromoperoxidase.

The Journal of organic chemistry

Andersson M, Willetts A, Allenmark S.
PMID: 11671985
J Org Chem. 1997 Nov 28;62(24):8455-8458. doi: 10.1021/jo9712456.

A vanadium-containing bromoperoxidase (VBrPO) from the alga Corallina officinalis has been shown to catalyze the stereoselective oxidation of some aromatic bicyclic sulfides to the corresponding (S)-sulfoxides in high (up to 91%) ee. Hydrogen peroxide was found to have a...

Nucleophilic epoxidation of alpha'-hydroxy vinyl sulfoxides.

The Journal of organic chemistry

Fernández de la Pradilla R, Fernández J, Manzano P, Méndez P, Priego J, Tortosa M, Viso A, Martínez-Ripoll M, Rodríguez A.
PMID: 12423147
J Org Chem. 2002 Nov 15;67(23):8166-77. doi: 10.1021/jo026182s.

The nucleophilic epoxidation of a variety of alpha'-(1-hydroxyalkyl) vinyl sulfones and sulfoxides has been studied. The sulfones give rise to anti oxiranes with modest (E) or excellent (Z) selectivities and in good yields. The (E)-sulfoxides display low reactivity within...

Showing 13 to 24 of 556 entries