593284-15-2

Upstream product

• 100-39-0 benzyl bromide 
• 438588-60-4 2-((1R,2R)-2-aminocyclohexyl)isoindoline-1,3-dione 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 915221-98-6 5-[1-((1R,2R)-2-Benzylamino-cyclohexylamino)-ethylidene]-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 915222-02-5 5-[1-((1R,2R)-2-Amino-cyclohexylamino)-ethylidene]-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 915222-03-6 5-[1-((1R,2R)-2-Dibenzylamino-cyclohexylamino)-ethylidene]-1,3-dimethyl-pyrimidine-2,4,6-trione 

Downstream Products

• 919112-98-4 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dibenzylamino)cyclohexyl}urea 
• 1352143-60-2 (1R,2R)-N,N-dibenzyl-1,2-diaminocyclohexane triflate 

Relevant academic research and scientific papers

A new chiral primary-tertiary diamine-Bronsted acid salt organocatalyst for the highly enantioselective direct anti-aldol and syn-Mannich reactions

A new primary-tertiary diamine catalyst is easily prepared in a few steps from inexpensive, commercially available, enantiopure materials. This organocatalyst can be effective catalyzed the direct asymmetric aldol and Mannich reactions. The anti-aldol products can be obtained with up to a 99:1 anti/syn ratio and >98 % ee, while the syn-Mannich products could be obtained with up to a 99:1 syn/anti ratio and >99 % ee. Catalyst 1c can be used efficiently on a large scale with the enantioselectivities of the anti-aldol and syn-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry.

Highly enantioselective aldol reactions using a tropos dibenz[c,e]azepine organocatalyst

The four-step synthesis of a chiral primary tertiary diamine salt, possessing a tropos dibenz[c,e]azepine ring is described. It is shown that 3.5-5 mol % of this salt is capable of promoting highly enantioselective crossed-aldol reactions between cyclohexanone and a series of aromatic aldehydes. In all cases, the aldol reactions proceed with high diastereoselectivity for the anti-aldol product. The outcome of crossed-aldol reactions involving other cyclic ketones and acyclic ketones are also described. All examples involving cyclic ketones result in selectivity for the anti-aldol products, whereas acyclic ketones were found to favour the syn-aldol products. A discussion on the role of the chiral primary tertiary diamine salt in the catalysis of the aldol reactions is also presented.

Direct monitoring of the asymmetric induction of solid-phase catalysis using circular dichroism: Diamine-CuI-catalyzed asymmetric Henry reaction

The direct approach: A new high-throughput screening system for analyzing the asymmetric induction in catalytic enantioselective synthesis couples solid-phase reactions with a circular dichroism detection system (see picture). Thus, direct monitoring of a

Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones

This article describes the synthesis of a library of structurally diverse bifunctional organocatalysts bearing both a quasi-Lewis acidic (thio)urea moiety and a Bronsted basic tertiary amine group. Sequential modification of the modular catalyst structure and subsequent screening of the compounds in the alcoholytic dynamic kinetic resolution (DKR) of azlactones revealed valuable structure-activity relationships. In particular, a "hit-structure" was identified which provides e.g. N-benzoyl-tert-leucine allyl ester in an excellent enantiomeric excess of 95%. The Royal Society of Chemistry 2006.

Facile monoprotection of trans-1,2-diaminocyclohexane

A new method of monoprotection of C2-symmetric trans-1,2-diaminocyclohexane as the N-phthaloyl, N-tetrachlorophthaloyl or N-1,8-naphthaloyl derivative is presented. The first two derivatives are obtained with high yields and can be readily transformed into other unsymmetrical derivatives of trans-1,2-diaminocyclohexane.