123820-99-5

Upstream product

• 28357-11-1 (+)-3R-exo-hydroxycamphor 
• 100-46-9 benzylamine 
• 10334-26-6 (R)-camphorquinone 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 193754-20-0 exo-2-hydroxyiminobornan-3-ol 

Downstream Products

• 123821-00-1 (1R,2S,3R,exo)-N-benzyl-2-amino-3-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptane 
• 159849-35-1 (1S,2R,6S,7R,exo)-N-cinnamoyl-3-oxa-5-aza-7,10,10-trimethyltricyclo<5.2.1.0^2,6>decan-4-one 
• 123821-09-0 (1S,2R,6S,7R)-7,10,10-Trimethyl-4-((1S,6S)-3,4,6-trimethyl-cyclohex-3-enyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 123821-02-3 (Z)-N-((1R,2S,3R,4S)-3-Hydroxy-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-3-phenylsulfanyl-acrylamide 
• 129064-39-7 (1S,2R,6S,7R)-7,10,10-Trimethyl-4-((1S,2S,6S)-6-methyl-2-phenylsulfanyl-cyclohex-3-enyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 123924-27-6 (1S,2R,6S,7R)-7,10,10-Trimethyl-4-((Z)-2-phenylsulfanyl-vinyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 123821-04-5 (1S,2R,6S,7R)-4-((Z)-2-Benzenesulfonyl-vinyl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 123821-08-9 (1S,2R,6S,7R)-4-((1S,2R,3R,4R)-3-Benzenesulfonyl-bicyclo[2.2.1]hept-5-en-2-yl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 123821-08-9 (1S,2R,6S,7R)-4-((1R,2R,3R,4S)-3-Benzenesulfonyl-bicyclo[2.2.1]hept-5-en-2-yl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 123924-27-6 (1S,2R,6S,7R)-7,10,10-Trimethyl-4-((E)-2-phenylsulfanyl-vinyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 129064-42-2 (1S,2R,6S,7R)-4-((R)-3,4-Dimethyl-cyclohex-3-enyl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 123821-04-5 (1S,2R,6S,7R)-4-((E)-2-Benzenesulfonyl-vinyl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 129064-41-1 (1S,2R,6S,7R)-7,10,10-Trimethyl-4-(2-phenylsulfanyl-cyclohex-3-enyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 129064-45-5 Phosphoric acid diphenyl ester (1R,4R,5R)-5-((1S,2R,6S,7R)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-bicyclo[2.2.1]hept-2-en-2-yl ester 

Relevant academic research and scientific papers

CHIRAL α,β-UNSATURATED OXAZOLINES IN THE ASYMMETRIC DIELS-ALDER REACTION

α,β-Unsaturated oxazolines derived from (+)-camphor become powerful dienophiles in asymmetric Diels-Alder reaction after activation with trifluoroacetic anhydride.

A viable route to exo-2-benzyliminobornan-3-ol: A key intermediate in the synthesis of a chiral auxiliary

A new synthesis of the title compound 2 has been achieved in which benzylamine reacts with the novel hydroxy N-nitroimine 6 with concomitant evolution of nitrous oxide, whereas the published reaction between benzylamine and the corresponding ketone 4 does not occur reproducibly.

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..

α,β-unsaturated oxazolines, a powerful tool in asymmetric diels-alder cycloadditions

α,β-Unsaturated oxazolines 10, 12, and 16, activated with trifluoroacetic anhydride, proved to be very powerful dienophiles toward various dienes such as 17-23 including Danishefsky type diene. The reactions were performed generally between -100 and -20 °C and the diastereoselectivity is usually better than 90%.