66965-39-7

Upstream product

• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 21286-54-4 Camphorsulfonyl chloride 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 459124-78-8 (1R,4S)-2-[(1'S,4'R)-2-oxo-1-bornylcarbonyl]-2-aza-3-oxabicyclo[3.2.2]-8-nonene 
• 459124-75-5 (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid hydroxyamide 
• 459124-79-9 (1S,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbaldehyde 
• 139174-14-4 (1S,2R)-7,7-dimethyl-2-methoxybicyclo[2.2.1]heptane-1-carboxylic acid chloride 
• 464-78-8 (1S)-(+)-ketopinic acid 
• 64234-14-6 (-)-(1R)-7,7-dimethyl-2-oxo-1-norbornanecarboxylic acid 
• 21286-54-4 D-camphor-10-sulfonyl chloride 
• 87206-51-7 l-10-Chlorocamphor-10-sulfine 
• 464-78-8 (1S)-ketopinic acid 

Downstream Products

• 1000304-12-0 C₁₈H₂₃NO₃ 
• 872865-10-6 C₁₈H₂₃NO₃ 
• 1367830-85-0 (1S,4R)-1-{[4-(2-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-one 
• 1367830-87-2 (1S,4R)-1-{[4-(3-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-one 
• 1367830-73-6 (1S,2R,4R)-1-{[4-(2-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-ol 
• 1367830-76-9 (1S,2R,4R)-1-{[4-(3-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-o 
• 1187081-73-7 C₃₃H₃₁NO₂ 
• 144757-96-0 {[(1S,4R)-1-(2-Hydroxy-phenylcarbamoyl)-7,7-dimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-methyl}-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones

A number of new chiral bispidines containing monoterpenoid fragments have been ob-tained. The bispidines were studied as ligands for Ni-catalyzed addition of diethylzinc to chalcones. The conditions for chromatographic analysis by HPLC-UV were developed,

On the Diastereoselectivity of the Complexation of Ketopinic Acid-Derived 2-Acyloxy-1,3-cyclohexadienes and the Configurational Stability of Dienol-Fe(CO)3Complexes. A Case Study

In the course of an attempt to synthesize 2-acyloxycyclohexa-1,3-diene-Fe(CO)3 complexes in nonracemic form, we reinvestigated the "fully diastereoselective"Fe(CO)3 complexation of (S,S)-2-ketopinoyloxy-1,3-cyclohexadiene, which had been described by Yeh and co-workers (Organometallics 2001, 20, 289-295). However, after cleaving off the chiral auxiliary unit, we only obtained racemic complexes, also for a related substrate. For this reason, we performed control experiments to exclude possible racemization mechanisms and confirmed the configurational integrity of the dienol-Fe(CO)3 intermediates using stereochemically defined dihydrocarvone-derived complexes. We finally could show that the complexation described by Yeh actually proceeds without any detectable diastereoselectivity. At the end, the virtually inseparable diastereomers of the chiral complexation products could be distinguished by careful NMR and chiral HPLC analyses.

Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones

The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.

Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand

In this article, the design and synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding alcohols in high yields and enantioselectivities. The role of the mercapto group in the highly enantioselective 1,2-addition reaction of organozincs to aldehyde is also discussed.

Dual stereoselection in the addition of diethylzinc to benzaldehyde by using highly structurally close ligands

The screening of the catalytic activity in the diethylzinc reaction of a series of easily accessible (1S)-ketopinic-acid derived hydroxyamides, designed by key structure modifications of a parent highly active related bis(hydroxyamide), has allowed to fin

Unexpected efficiency of non-C2-symmetric bis(hydroxyamide)- based zinc-chelate catalysts

Asymmetric bis(hydroxyamide)-based zinc-chelate catalysts are able to promote the enantioselective addition of diethylzinc to benzaldehyde in the absence of titanium with yields and ees comparable, or inclusively superior, to their C2-symmetric

Exo-selective asymmetric inverse-electron demand hetero-diels-alder reaction catalyzed by Cu(II)-hydroxy oxazoline ligands

Cu(II) complexes of hydroxy oxazolines derived from (+)-(S)-ketopinic acid catalyze the asymmetric hetero-Diels-Alder cycloaddition of enol ethers and ,-unsaturated -keto esters. The reaction takes place with unprecedented exo selectivity providing 2,4-trans-disubstituted chiral 2,3-dihydropyrans with up to 88% ee. Georg Thieme Verlag Stuttgart ? New York.

Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to β-nitroalkenes

Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical αα-disubstituted ald

Highly diastereo- and enantioselective direct aldol reactions promoted by water-compatible organocatalysts bearing a pyrrolidinyl-camphor structural scaffold

Efficient synthetic routes have been developed for the synthesis of a series of pyrrolidinyl-camphor containing organocatalysts (1-10). Structural modifications were made by varying the stereo- and electronic properties of the camphor scaffold and the aromatic substituents. These readily tunable and amphiphilic organocatalysts were evaluated for the direct asymmetric aldol reaction of various aromatic aldehydes and cyclohexanone either in organic solvents or in the presence of water. The aldol reaction proceeded smoothly with excellent chemical yields (up to 99%), enantioselectivities (up to 99% ee), and anti-diastereoselectivities (up to 99:1) with a catalytical amount of the bifunctional organocatalysts (20 mol %) under optimal reaction conditions. Mechanistic transition models are proposed and the stereochemical bias of the asymmetric aldol reaction is presented.

Highly diastereoselective synthesis of pyrido[2,1-b][1,3]oxazin-4(6H)-one by intramolecular anodic oxidation

This paper describes a method for the intramolecular anodic oxidation of ω-hydroxyl amides. Products were obtained in acceptable yields from different starting materials using various applied currents, charge, and reactant concentrations. Compounds 1a and 1d afforded a single diastereomer in 67% yield when the applied current and reactant concentration were 100 mA and 0.04 M.