644958-86-1

Usage

Uses

Used in Organic Synthesis:
(1R,2R)-N,N'-Dimethyl-N,N'-bis(3,3-dimethylbutyl)cyclohexane-1,2-diamine is utilized as a chiral ligand in various catalytic reactions, such as asymmetric hydrogenation and hydroformylation. Its chiral nature allows for the selective formation of desired enantiomers, which is crucial in the synthesis of biologically active compounds.
Used in Pharmaceutical Industry:
Due to its potential for inducing stereo-selective reactions, (1R,2R)-N,N'-Dimethyl-N,N'-bis(3,3-dimethylbutyl)cyclohexane-1,2-diamine is studied for its application in the development of pharmaceuticals. The ability to control the stereochemistry of synthesized compounds can lead to the creation of more effective and selective drugs with fewer side effects.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, (1R,2R)-N,N'-Dimethyl-N,N'-bis(3,3-dimethylbutyl)cyclohexane-1,2-diamine is being explored for its potential in the synthesis of chiral agrochemicals. The control over stereochemistry can result in the production of more targeted and environmentally friendly pesticides and other agricultural chemicals.

InChI:InChI=1/C20H42N2/c1-19(2,3)13-15-21(7)17-11-9-10-12-18(17)22(8)16-14-20(4,5)6/h17-18H,9-16H2,1-8H3/t17-,18-/m1/s1

Upstream product

• 2987-16-8 3,3-dimethylbutyrylaldehyde 
• 68737-65-5 (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane 
• 50-00-0 formaldehyd 
• 189152-00-9 (1S,2S)-(+)-N,N'-bis(3,3-dimethylbutyl)-1,2-cyclohexanediamine 

Relevant academic research and scientific papers

Organocatalytic Knoevenagel condensation by chiral: C 2-symmetric tertiary diamines

The efficient Knoevenagel condensation catalyzed by (1S,2S)-1,2-diaminocyclohexane derivatives is presented and investigated. Various aliphatic aldehydes undergo condensation with active methylene compounds to yield the corresponding products in high yields. α-Branched aldehydes were found to be efficiently converted to the corresponding enantiomerically enriched products by using these chiral tertiary diamine catalysts.

A new sparteine surrogate for asymmetric deprotonation of N-Boc pyrrolidine

(Chemical Equation Presented) The s-BuLi complex of a cyclohexane-derived diamine is as efficient as s-BuLi/(-)-sparteine for the asymmetric deprotonation of N-Boc pyrrolidine. This is the first example of high enantioselectivity using a non-sparteine-like diamine in such reactions. The ( S, S)-diamine is a useful (+)-sparteine surrogate and was utilized in short syntheses of (-)-indolizidine 167B and an intermediate for the synthesis of the CCK antagonist (+)-RP 66803.

Enantioselective addition of methyllithium to aromatic imines catalyzed by C2 symmetric tertiary diamines

Enantioselective addition of methyllithium to aromatic imines catalyzed by C2 symmetric tertiary diamines is described. Eleven diamines have been tested, for which dramatic effect of the nitrogen substitution has been observed. Diamines bearing hindered group close to the nitrogen led to racemic product while homologous hindered diamines led to the best results. Enantiomeric excess up to 74% could be achieved. An explanation of the absolute configuration of the product obtained is given considering the mechanism of the reaction.

Effect of ligand structure on the asymmetric cyclization of achiral olefinic organolithiums

The ability of a large and chemically diverse set of 30 chiral ligands to effect asymmetric cyclization of 2-(N,N-diallylamino)phenyllithium (1), derived from N,N-diallyl-2-bromoaniline (2) by low-temperature lithium-bromine exchange, has been investigated in an attempt to elucidate the structural motifs required to provide high enantiofacial selectivity in the ring closure. Although none of the ligands examined in this study afforded 1-allyl-3-methylindoline in significantly higher ee than previously observed for the cyclization of 1 in the presence of the benchmark ligand (-)-sparteine, several ligands, structurally unrelated to sparteine and available in either enantiomeric form, were found to match the utility of (-)-sparteine in this chemistry.

Conceptually new chiral tertiary C2 symmetric diamines in asymmetric synthesis

New chiral diamines were prepared, based on the cyclohexane diamine core. The two different substituents on each nitrogen allow this heteroatom to become a stereogenic center upon chelation with a metal, such as lithium. The enantioselective addition of MeLi to imines, with ee's up to 68%, illustrates the validity of this concept.