159849-35-1

Upstream product

• 102-92-1 cinnamoyl chloride 
• 159849-26-0 (1S,2R,6S,7R,exo)-3-oxa-5-aza-7,10,10-trimethyltricyclo<5.2.1.0^2,6>decan-4-one 
• 102-92-1 Cinnamoyl chloride 
• 28357-11-1 (+)-3R-exo-hydroxycamphor 
• 159990-17-7 (1S,2R,6S,7R)-7,10,10-Trimethyl-5-((S)-2-methyl-3-phenyl-propionyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one 
• 159849-30-6 (1S,2R,6S,7R)-7,10,10-Trimethyl-5-((R)-2-methyl-3-phenyl-propionyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one 
• 123820-99-5 (1R,3R,exo)-N-benzyl-2-imino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane 
• 123821-00-1 (1R,2S,3R,exo)-N-benzyl-2-amino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane 
• 123879-93-6 exo,exo-2-amino-3-hydroxy-camphor 
• 10334-26-6 (R)-camphorquinone 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 

Relevant academic research and scientific papers

Diastereoselective ru-catalyzed cross-metathesis-dihydroxylation sequence. An efficient approach toward enantiomerically enriched syn-diols

(Chemical Equation Presented) Sequential catalysis has evolved as a powerful concept within the past years and allows the more efficient use of catalytically active expensive transition metals in organic synthesis. In this paper we present the stereoselective cross-metathesis-dihydroxylation of various olefins with chiral auxiliary substituted acrylamides. The chiral information (i.e., the auxiliary) introduced in the metathesis reactions allows for a stereoselective subsequent RuO4-catalyzed dihydroxylation. The sequence is concluded by an unusual kinetic resolution of the diastereomeric diols obtained in the oxidation reaction. As a consequence a variety of structurally diverse enantiomerically enriched diols are obtained. To the best of our knowledge the results summarized in this paper represent the first highly efficient diastereoselective RuO4-catalyzed oxidation.

Asymmetric Diels-Alder reactions employing modified camphor-derived oxazolidin-2-one chiral auxiliaries

Transposition of the dormant methyl group from C-1 in chiral oxazolidin-2-one 2 to C-7 in a six step synthetic sequence from (1R)-camphore 5 creates a novel transfigomer 4 with sufficient π-topological bias to induce excellent levels of asymmetric induction in Lewis-acid catalysed Diels-Alder reactions of its α, β-unsaturated carboximide derivatives with cyclopentadiene. Further modification of 4 by replacement of the C-7 methyl group with an ethyl substituent raises the level of diastereoselectivity for the acrylate derivative 11a from 81 to > 95% d.e..

exo,exo-2-Amino-3-borneol-derived Oxazolidinone as a New Chiral Auxiliary for use in Asymmetric Transformations

N-Acylimides derived from exo,exo-2-amino-3-borneol when subjected to alkylation, Diels-Alder reaction, and conjugate additions afford the corresponding products with a high level of asymmetric induction, particularly in those cases of inherent poor diastereofacial selectivity.