103668-49-1Relevant articles and documents
Reduction of β-hydroxyketones by Sml2/H2O/ Et3N
Davis, Todd A.,Chopade, Pramod R.,Hilmersson, Goeran,Flowers II, Robert A.
, p. 119 - 122 (2007/10/03)
(Chemical Equation Presented) Reduction of a series of β- hydroxyketones by Sml2/H2O/Et3N provided 1,3-diols in quantitative yields. The reactions were exceedingly clean with no byproduct formation, negating the need for f
Stereospecific conversion of (1R*,3S*)- And (1R*,3A*)-3-cyclohexyl-l-phenylpropane-l,3-diol into the corresponding 2,4-disubstituted oxetanes
Aftab, Tajassus,Carter, Christabel,Christlieb, Martin,Hart, Jennifer,Nelson, Adam
, p. 711 - 722 (2007/10/03)
Conversion of two diastereoisomeric 1,3-dioIs (3-cyclohexyl-l-phenylpropane-l,3-diol) into orthoesters was followed' by treatment with acetyl bromide. The 1,3-bromo acetates (acetic acid 3-bromo-l-cycIohexyl-3-phenyIpropyl esters) were obtained with complete inversion of configuration at a benzylic site. Methanolysis of the bromo acetates, followed by ring-closure, resulted in a second inversion of configuration at a benzylic site to give the corresponding oxetanes with overall retention of configuration. The Royal Society of Chemistry 2000.
Simple metal alkoxides as effective catalysts for the hetero-aldol-Tishchenko reaction
Mascarenhas, Cheryl M.,Duffey, Matthew O.,Liu, Shih-Yuan,Morken, James P.
, p. 1427 - 1429 (2008/02/09)
(equation presented) This paper reports the utility of simple metal alkoxides for the catalytic, stereoselective hetero-aldol-Tishchenko reaction (eq 1). Choice of metal alkoxide is crucial to achieving high efficiency and stereoselectivity. Whereas NaO-t
Diastereoselective reduction of β-hydroxyketones with amineboranes in the presence of lithium perchlorate
Narayana, Chatla,Reddy, M. Rama,Hair, Max,Kabalka, George W.
, p. 7705 - 7708 (2007/10/03)
The reduction of β-hydroxyketones with amineboranes in the presence of lithium perchlorate produces the corresponding anti 1,3-diols as major products.
In search of open-chain 1,3-stereocontrol
Barbero, Asun,Blakemore, David C.,Fleming, Ian,Wesley, Robert N.
, p. 1329 - 1352 (2007/10/03)
Methylation of methyl 4-phenylpentanoate 25 gives the diastereoisomers methyl (2RS,4SR)-2-methyl-4-phenylpentanoate 26 and methyl (2RS,4RS)- 2-methyl-4-phenylpentanoate 27 in a ratio of 44:56. The aldehydes 3-dimethyl(phenyl)silylbutanal 28, 3-dimethyl(ph
Chiral Organometallic Reagents, I. Stereoselective Exchange of Diastereotopic Bromine Atoms by Lithium in 1,1-Dibromo-3-(trimethylsilyloxy)alkanes
Hoffmann, Reinhard W.,Bewersdorf, Martin,Krueger, Michael,Mikolaiski, Wolfgang,Stuermer, Rainer
, p. 1243 - 1252 (2007/10/02)
Bromine-lithium exchange in 1,1-dibromo-3-(trimethylsilyloxy)alkanes 4 and 6 affords the carbenoids 8 and 14, which have been added to ketones, aldehydes, arylboronates, and silylating agents.Diastereoselectivity in the generation and trapping of the carb
STUDIES ON THE DIASTEREOSELECTIVE REDUCTION OF β-HYDROXY KETONES TO 1,3-DIOLS WITH COMMON HYDRIDE REAGENTS
Bonini, Carlo,Bianco, Armandodoriano,Fabio,Romano Di,Mecozzi, Sandro,Proposito, Alessandro,Righi, Giuliana
, p. 75 - 80 (2007/10/02)
Some common reducing agents were employed in the diastereoselective reduction of several β-hydroxy ketones to their corresponding syn-1,3-diols.The use of NaBH4 with a Ti(IV) chelating species produced syn diols with a moderate to good selectivity significantly depending upon the reaction conditions chosen (solvent, temperature, nature of the titanium species).The use of LiAlH4 at low temperature, in the presence of LiI, showed a high selectivity for reduction to syn diols, thus demonstrating a possible chelating role of lithium.Some interesting preliminary results have been also obtained in the diastereoselective reduction of MEM-protected β-alkoxy ketones.
1,3-SYN DIASTEREOSELECTIVE REDUCTION OF β-HYDROXYKETONES WITH DIISOBUTYLALUMINUM HYDRIDE AND TRIBUTYLTIN HYDRIDE
Kiyooka, Syun-ichi,Kuroda, Hisanori,Shimasaki, Yayoi
, p. 3009 - 3012 (2007/10/02)
1,3-Syn diastereofacial selectivity (12 : 1) has been achieved in a facile reduction of β-hydroxyketones with DIBAL-H.Tributyltin hydride also has shown 1,3-syn selectivity.