100190-34-9

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 121958-27-8 C₁₈H₂₂NO₂^(1-)*Li⁽¹⁺⁾ 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 19980-34-8 trimethyl-(2-methyl-cyclopent-1-enyloxy)-silane 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 121959-66-8 (R)-bis(1-phenyl-2-methoxyethyl)amine 
• 121868-97-1 (R)-2-((R)-2-Methoxy-1-phenyl-ethylamino)-2-phenyl-ethanol 
• 56613-80-0 D-2-phenylglycinol 

Downstream Products

• 128298-81-7 (2S,4S)-2-hydroxy-4-tert-butylcyclohexanone 
• 128298-82-8 (2R,4S)-4-tert-Butyl-2-hydroxy-cyclohexanone 
• 10347-88-3 (3S)-3-tert-butylhexanedionic acid 
• 65970-71-0 (S)-3-tert-butylhexan-1,6-dioic acid 
• 16099-37-9 2-benzyl-4-tert-butylcyclohexanone 
• 74365-82-5 (2S,4R)-(+)-2-methyl-4-tert-butylcyclohexanone 
• 148810-45-1 cis-2-Methyl-4-tert.-butyl-cyclohexanon-⁽¹⁾ 
• 148810-44-0 trans-2-Methyl-4-tert-butylcyclohexanon 
• 74365-81-4 (2R,4R)-(+)-2-methyl-4-tert-butylcyclohexanone 
• 128226-87-9 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,5R)-5-tert-butyl-2-oxo-cyclohexyl ester 
• 128658-62-8 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,5S)-5-tert-butyl-2-oxo-cyclohexyl ester 

Relevant academic research and scientific papers

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 of 4-tert-butylcyclohexanone by conformationally constrained chiral lithium amide bases

Conformationally rigid chiral lithium amides based on a tetrahydroisoquinoline motif have been prepared bearing a range of substituents at C1 and C3. These bases were tested in the asymmetric deprotonation reaction of 4-tert-butylcyclohexanone. Although t

Optimisation of a lithium magnesiate for use in the non-cryogenic asymmetric deprotonation of prochiral ketones

A study has been conducted to determine whether lithium magnesiates are feasible candidates for the enantioselective deprotonation of 4-alkylcyclohexanones. The commercially available chiral amine (+)-bis[(R)-1-phenylethyl]amine (2-H) was utilised to indu

New chiral ferrocenyl building blocks for asymmetric reactions

The new C2-symmetrical ferrocenyl amines 2 and 3 are easily prepared starting from the ketones 4. Their utility is demonstrated for enantioselective deprotonation reactions and highly diastereoselective alkylations of the amides 7.

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

Enantioselective synthesis of cyclohexenylalkenes by asymmetric deprotonation of 4-tert-butylcyclohexanone followed by O-nonaflation and heck couplings

Formation of (S)-4-tert-butylcyclohex-1-enyl nonaflate 4 by reaction with nonafluorobutanesulfonyl fluoride was found to be highly enantioselective both from (S)-4-tert-butyl-1-(trimethyl-siloxy)cyclohexene 3 and from the corresponding lithium enolate 2. The latter was generated by kinetic deprotonation of 4-tert-butylcyclohexanone 1 with lithium (R,R′)-bis(1-phenylethyl)amide as enantiopure base. A number of functionalized 2-(4-tert-butylcyclohex-1-enyl)alkenes 6 were prepared with roughly 90% enantiomeric excess from trimethylsilyl enol ether 3 using a one-pot nonaflation/Heck reaction sequence.

An Enhancement of Enantioselectivity in Chiral Lithium Amide Deprotonations Due to Lithium Chloride

Substantial improvements in the enantiomeric excess of products obtained from chiral base-mediated reactions of prochiral ketones under external quench (EQ) conditions are observed if the deprotonation is carried out in the presence of added LiCl.

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.

Stereoselective reactions. 29. Lithium-hydrogen interchange between achiral tridentate lithium amides and chiral bidentate amines. An approach to catalytic enantioselective

1H-NMR spectral studies have shown that lithium-hydrogen interchange between a chiral bidentate amine ((R)-3b) and an achiral tridentate lithium amide (5a) occurs rapidly in THF, favoring the exclusive formation of a chiral bidentate lithium am

Stereoselective reactions. 28. Effects of the alkyl group at the amide nitrogen of chiral bidentate lithium amides on enantioselective deprotonation reaction

Enantioselective deprotonation of 4-substituted cyclohexanones (1a-d) by chiral bidentate lithium amides ((R)-2a-j) having an alkyl- or a fluoroalkyl substituent at the amide nitrogen was examined. (R)-2i having a 2,2,2-trifluoroethyl group at the amide nitrogen was found to be an excellent chiral base for the present deprotonation reaction. Structures of (R)-2i in solution and solid state are discussed.