103138-17-6

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 766-42-7 cis-2,6-dimethylcyclohexanone 
• 2816-57-1 2,6-dimethylcyclohexanone 

Downstream Products

• 114247-77-7 (2S,6S)-2,6-dimethyl-2-hydroxycyclohexanone 
• 103189-93-1 (2R,6R)-2-Hydroxy-2,6-dimethyl-cyclohexanone 
• 103189-92-0 (+/-)-2r-bromo-2,6t-dimethyl-cyclohexanone 
• 128658-61-7 (2S,6S)-2-bromo-2,6-dimethylcyclohexanone 

Relevant academic research and scientific papers

Synthesis of polymer-supported chiral lithium amide bases and application in asymmetric deprotonation of prochiral cyclic ketones

Polymer-supported chiral amines were effectively prepared from amino acid derivatives and Merrifield resin. Treatment of polymer-supported amines with n-butyllithium gave the corresponding polymer-suppported chiral lithium amide bases, which were tested i

Development of chiral heteroleptic magnesium amides; Asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates

A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An ef

Novel enantiomerically pure heteroleptic magnesium complexes for use in enantioselective deprotonation reactions

Two classes of heteroleptic magnesium complexes, alkylmagnesium amides RMgNR2 and aryloxymagnesium amides ROMgNR2, have been prepared and subsequently shown to be efficient bases in the enantioselective deprotonation of substituted c

Magnesium amide base-mediated enantioselective deprotonation processes

A novel homochiral magnesium bisamide has been readily prepared and, following careful optimisation, this species has been shown to react efficiently with a series of prochiral 4-substituted cyclohexanones in the presence of TMSCl to give the corresponding silyl enol ethers in enantiomeric ratios of up to 95:5. Additionally, the same chiral base system has been shown to be highly effective in the desymmetrisation of cis-2,6-disubstituted cyclohexanones, providing excellent levels of both conversion and enantioselection (up to >99.5:0.5 er). Furthermore, the magnesium bisamide has also been shown to mediate a kinetic resolution process with the corresponding trans-disubstituted substrates, allowing access to enantioenriched enol ethers and ketones.

Enantioselective deprotonation of 2,6-disubstituted cyclohexanones with a homochiral magnesium amide base and the observation of a novel kinetic resolution process

A recently developed homochiral magnesium amide base has been shown to be highly effective in the asymmetric deprotonation of cis-2,6-disubstituted cyclohexanones, affording excellent levels of both conversion and enantioselection (up to >99.5:0.5 e.r.).

Effect of amine structure and reaction additives on enantioselective deprotonations mediated by homochiral magnesium amide bases

A series of novel, optically pure, Mg-bisamides have been prepared and, in turn, used to mediate enantioselective deprotonations of conformationally locked ketones. The new bases exhibit a wide range of selectivities, from poor to excellent (up to 95:5 e.

Enantioselective deprotonation reactions using a novel homochiral magnesium amide base

A novel homochiral magnesium bisamide base system has been prepared and reacted with a series of prochiral ketones in the presence of TMSCl to give efficient formation of the corresponding enol ethers in enantiomeric ratios of up to 95:5.

ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES

A number of chiral secondary amines have been prepared and used as precursors to the corresponding chiral lithium amide bases.Treatment of either cis-2,6-dimethylcyclohexanone or 4-tert-butylcyclohexanone with a chiral lithium amide, followed by electrophilic quench, gives chiral products in up to 88 percent enantiomeric excess.The results with 4-tert-butylcyclohexanone are in disagreement with an earlier literature report, giving products of lower enantiomeric excess but higher optical rotation.

Asymmetric Deprotonation: A New Route to Chiral Compounds

Enantioselective deprotonation of symmetrically substituted ketones under kinetically controlled conditions provides chiral products in up to 74percent enantiomeric excess.