16099-67-5Relevant articles and documents
Chiral auxiliaries and their use in the synthesis of chiral molecules
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, (2008/06/13)
Chiral imidazolidones and imidazolidinethiones having the general formula: STR1 where (a) Z is either oxygen or sulphur (b) the R groups are independently selected from hydrogen or R2 CO where R2 is C1 to C10 alkyl, C2 to C10 alkenyl or benzyl and (c) the two R1 groups are either (1) identical groups selected from C1 to C10 alkyl, phenyl or C1 to C6 alkyl or alkoxy substituted phenyl or (2) such that together they form an alkylene group of formula --(CH2)n -- where n=3 to 8. Most preferred are those compounds where both R groups are R2 CO and there is a C2 axis of symmetry running along the CZ double bond. Compounds of formula (I) where at least one R group is R2 CO are efficient chiral auxiliaries for a range of asymmetric electrophilic substitution reactions when used in homochiral form. As such they are important tools for synthesising a range of chiral pharmaceuticals, agrochemicals and the like.
Bifunctional chiral auxiliaries 2: The synthesis of 1,3-diacylimidazolidin-2-ones from 1,2-diamines
Davies,Mortlock
, p. 4791 - 4794 (2007/10/02)
The title compounds are readily prepared in three steps via the corresponding 1,3-diacylimidazolidine-2-thiones. The final step involves the novel use of mercury (II) acetate for the conversion of thioureas to ureas.
