619-52-3Relevant articles and documents
(-)-Menthol as a source of new N,N-diamine ligands for asymmetric transfer hydrogenation
Roszkowski, Piotr,Maurin, Jan K.,Czarnocki, Zbigniew
supporting information, p. 2184 - 2188 (2018/05/07)
The synthesis of new chiral N-monotosylated-1,2-diamines based on the (-)-menthol skeleton is presented. The elimination of HCl from neomenthyl chloride obtained from an Appel reaction led to p-menth-3-ene in excellent yield. Further functionalization of the double bond in p-menth-3-ene with chloramine-T gave the corresponding N-tosylaziridines, which upon reaction with sodium azide and subsequent reduction of the azide functional group, formed the 1,2-diamine system. The synthesized chiral ligands proved effective in the asymmetric transfer hydrogenation of aromatic ketones and an endocyclic imine.
Clarification of the stereochemical course of nucleophilic substitution of arylsulfonate-based nucleophile assisting leaving groups
Braddock, D. Christopher,Pouwer, Rebecca H.,Burton, Jonathan W.,Broadwith, Phillip
experimental part, p. 6042 - 6049 (2009/12/24)
(Chemical Equation Presented) Secondary alcohols modified as tosylates, PEG-sulfonates, or quisylates undergo inversion of configuration at the reacting center when treated with lithium halide in acetone at reflux, where the PEG-sulfonates and quisylates are substantially more reactive. In sterically hindered cases, elimination is a competing process. In contrast, when treated with TiCl4, simple secondary sulfonates give chloride products with partial inversion of configuration. Any observed retention of configuration in a given alkyl sulfonate substrate under these conditions is likely due to neighboring group participation or diastereoselective attack on a carbocation (or ion pair) rather than an SNi mechanism.
Synthesis of the promising chiral synthon isopropyl-4R-methyl-6- iodohexanoate from L-(-)-menthol
Ishmuratov,Yakovleva,Ganieva,Muslukhov,Tolstikov
, p. 41 - 44 (2007/10/03)
A synthesis of the promising optically pure synthon isopropyl-4R-methyl-6- iodohexanoate based on ozonolytic transformation of the product of regiospecific dehydratation of L-(-)-menthol, (R)-p-menth-3-ene, into 2,6R-dimethyl-8- hydroxyoctan-3-one was proposed. 2005 Springer Science+Business Media, Inc.