TBD-catalyzed α-sulfenylation of cyclic ketones: Desymmetrization of 4-substituted cyclohexanones
A low loading of triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzes the α-sulfenylation reaction of ketones employing tetramethylthiuram disulfide (TMTDS) as electrophilic reagent. This methodology is mild, effective and straightforward, rendering the desired products in high yield. Prochiral 4-substituted cyclohexanones can be desymmetrized with remarkable diastereoselectivity following this protocol. The dithiocarbamoyl function was shown to be easily removed upon reduction, affording thiols (1-mercaptan-2-ols).
Direct organocatalytic -sulfenylation of aldehydes and ketones with tetramethylthiuram disulfide
The direct pyrrolidine-catalyzed -sulfenylation of aldehydes and ketones with the commercially available, very cheap chemical tetramethylthiuram disulfide (thiram) is described. The dithiocarbamoyl derivatives are obtained in good to excellent yields (47-
Enders, Dieter,Rembiak, Andreas,Liebich, Jens X.
scheme or table
p. 281 - 286
(2011/03/18)
ORGANOSULFUR TRANSFER WITH DISULFIDES IN THE PRESENCE OF CCl4
Thiols and protic nucleophiles undergo sulfur-element bond formation in the presence of CCl4/ base.Sulfenylation of CH-acidic compounds with thiols occur via disulfides, formed in a preliminary step.Uses and advantages of this organosulfur transfer are de
Wenschuh, Eberhard,Hesselbarth, Frank
p. 133 - 136
(2007/10/02)
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