133867-57-9Relevant academic research and scientific papers
Asymmetric Radical Reaction in the Coordination Sphere. IV. Ruthenium(II)-Catalyzed Asymmetric Addition of Sulfonyl Chloride to 1-Phenylpropene
Kameyama, Masayuki,Kamigata, Nobumasa
, p. 648 - 650 (1989)
The asymmetric addition of methane- and p-toluenesulfonyl chloride to 1-phenylpropene catalyzed by Ru2Cl43 affords optically active 1:1 adducts, (+)-(1R,2RS)-1-chloro-2-methylsulfonyl-1-phenylpropane (2) and (+)-(1R,2RS)-1-chloro-1-phenyl-2-tosy
Acetalsulfonate derivative, process for producing the same, and process for producing styrene oxide derivative
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Page/Page column 10-11, (2010/01/31)
There are provided an acetalsulfonate derivative useful as an intermediate for medicines and agricultural chemicals, a process for industrially producing the derivative, and a process for industrially producing a styrene oxide derivative from the acetalsulfonate derivative or from a mandelic acid derivative. A process for producing an acetalsulfonate derivative which comprises a first step of esterifying a mandelic acid derivative to form a mandelic ester derivative, a second step of protecting the mandelic ester derivative by an acetal to form an acetal derivative, a third step of reducing the acetal derivative to form an ethanediol derivative and a fourth step of reacting the ethanediol derivative with a sulfonyl chloride derivative. A process for producing a styrene oxide derivative which comprises a deprotecting step of deacetalizing the acetalsulfonate derivative and a step of epoxidizing the sulfonate derivative obtained in the deprotecting step with the aid of a base catalyst.
Zirconium cation coordination in the borohydride-mediated synthesis of β-hydroxy-N-alkoxylamines
Williams, David R,Benbow, John W,Sattleberg, Thomas R,Ihle, David C
, p. 8597 - 8601 (2007/10/03)
Hydride reductions of oxime ethers to hydroxylamine derivatives are facilitated by the participation of neighboring hydroxyl groups. Precomplexation with zirconium cation in ether-methylene chloride solutions is effective for selective C=N bond reduction. The course for stereochemical control is dictated by Lewis acid coordination complexes of E- and Z-oximino ethers which lead to the preferred diastereofacial delivery of external hydride.
trans-1,3-Dithiane-1,3-Dioxide, a New Chiral Acyl Anion Equivalent for the Preparation of Masked Activated Acids: Application to the Synthesis of α-Hydroxy Acid Derivatives
Aggarwal, Varinder K.,Thomas, Abraham,Franklin, Richard J.
, p. 1653 - 1654 (2007/10/02)
trans-1,3-Dithiane-1,3-dioxide reacts with high diastereoselectivity with aromatic aldehydes and the 1,3-dithiane-1,3-dioxide moiety can be easily converted to a thiolester without racemisation by carrying out a Pummerer reaction; the thiolester is a group that can be readily transformed into acids, esters, amides, ketones and aldehydes.
Enantioselective Protonation of Samarium Enolates by a C2-Symmetric Chiral Diol
Takeuchi, Seiji,Ohira, Akiko,Miyoshi, Norikazu,Mashio, Hajime,Ohgo, Yoshiaki
, p. 1763 - 1780 (2007/10/02)
High enantioselectivity (up to 97percentee) have been achieved in the protonation of samarium enolates which were generated by SmI2-mediated cross-coupling reaction between unsymmetrical dialkylketene and allyl iodide, using, using a C2-symmetr
Recognition by New Symmetrically Substituted Chiral Diphenyl- and Di-tert-butylpyridino-18-crown-6 and Asymmetrically Substituted Chiral Dimethylpyridino-18-crown-6 Ligands of the Enantiomers of Various Organic Ammonium Perchlorates
Huszthy, Peter,Bradshaw, Jerald S.,Zhu, Cheng Y.,Izatt, Reed M.,Lifson, Shneior
, p. 3330 - 3336 (2007/10/02)
Three new chiral pyridino-18-crown-6 ligands have been prepared.These ligands contain either two phenyl, two tert-butyl, or two methyl substituents on chiral macroring carbon atoms.The chiral di-tert-butyl-substituted diester crown analogue was also prepared.The starting chiral di-tert-butyl-substituted tetraethylene glycol needed to prepare the two di-tert-butyl-substituted crowns was obtained from chiral tert-butyl-1,2-ethanediol, which was resolved from its bis(hydrogen phthalate) brucine salt.A high degree of chiral recognition in CD2Cl2 of the enantiomers of ammonium perchlorate (NapEt) was shown by the diphenyl- and di-tert-butyl-substituted crowns as measured by differences in the free energy of avtivation (ΔGc*) values determined by temperature dependent 1H NMR spectroscopy.The diphenyl- and di-tert-butyl-substituted crowns also exhibited high chiral recognition for the enantiomers of NapEt and other chiral organic ammonium salts in methanol and methanol-chloroform mixtures as shown by a large difference in the log K values determined by a direct 1H NMR technique.
Asymmetric Radical Reaction in the Coordination Sphere. 2. Asymmetric Addition of Alkane- and Arenesulfonyl Chlorides to Olefins Catalyzed by a Ruthenium(II)-Phosphine Complex with Chiral Ligands
Kameyama, Masayuki,Kamigata, Nobumasa,Kobayashi, Michio
, p. 3312 - 3316 (2007/10/02)
The addition of arenesulfonyl chlorides to styrene in the presence of a catalytic amount of a ruthenium(II) complex with chiral phosphine ligands, Ru2Cl43 or Ru2Cl43, proceeds under mild conditions to give optically active 1:1 adducts,
