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Titanium reagents, chirally modified enantioselective addition

The Orsay group found serendipitously that methyl p-tolyl sulfide was oxidized to methyl p-toly 1 sulfoxide with high enantiomeric purity (80-90% ee) when the Sharpless reagent was modified by addition of 1 mole equiv. of water [16,17]. The story of this discovery was described in a review [19], Sharpless conditions gave racemic sulfoxide and sulfone. Careful optimization of the stoichiometry of the titanium complex in the oxidation of p-tolyl sulfide led to the selection of Ti(0iPr)4/(7 ,7 )-DET/H20 (1 2 1) combination as the standard system [ 17]. In the beginning of their investigations, the standard conditions implied a stoichiometric amount of the chiral titanium complex with respect to the prochiral sulfide [16,17,20-23]. Later, proper conditions were found, which decreased the amount of the titanium complex without too much alteration of the enantioselectivity [24,25],... [Pg.328]

CHIRALLY MODIFIED TITANIUM REAGENTS ENANTIOSELECTIVE ADDITION... [Pg.165]


See other pages where Titanium reagents, chirally modified enantioselective addition is mentioned: [Pg.158]    [Pg.42]    [Pg.225]   


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Chiral additives

Chiral enantioselectivity

Chiral modifiers

Chiral reagent

Chirality modifiers

Chirally enantioselectivity

Enantioselective additions

Enantioselective reagents

Enantioselectivity chiral additives

Reagent addition

Titanium chirality

Titanium reagents

Titanium reagents, chirally modified

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