95340-90-2

Upstream product

• 5062-98-6 cis-endo-2,3-bis(hydroxymethyl)bicyclo<2.2.1>heptane 
• 95340-88-8 (3aS,4R,7S,7aR)-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one 
• 17812-27-0 cis-5-norbornene-endo-2,3-dicarboxylic anhydride 
• 162362-12-1 (1R,2R,3S,4S)-7-Oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester 3-((1R,2S)-2-phenyl-cyclohexyl) ester 
• 29910-09-6 N-phenyltricyclo[2.2.1]heptane-2β,6β-dicarboximide 
• 167390-18-3 C₄₀H₄₇NO₆S 
• 542-92-7 cyclopenta-1,3-diene 
• 129-64-6 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 
• 121701-13-1 (1S,2S,3R,4R)-2-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester 
• 121611-73-2 (1R,2R,3S,4S)-2-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester 
• 129887-41-8 (+)-(1R,R_S)-2-exo-<((1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptan-1-yl)methylsulphinyl>-3-endo-hydroxymethylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid lactone 
• 96243-73-1 (1R,2S,3R,4S)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 941567-71-1 (1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol 
• 116877-11-3 (1S,2S,3R,4R)-3-Hydroxymethyl-bicyclo[2.2.1]heptane-2-carbaldehyde 

Downstream Products

• 128208-11-7 (2S,3R)-cis-endo-3-(phenylthiomethyl)bicyclo<2.2.1>heptane-2-carboxylic acid 
• 128208-12-8 (2S,3R)-cis-endo-3-(phenylsulfonylmethyl)bicyclo<2.2.1>heptane-2-carboxylic acid 
• 128208-18-4 (1S,2S,3R,4R)-3-Benzenesulfonylmethyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester 
• 128208-16-2 (1S,2S,3R,4R)-3-Phenylsulfanylmethyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Catalytic asymmetric oxidative lactonizations of meso-diols using a chiral iridium complex

A chiral amino alcohol/Ir complex catalyzes the asymmetric oxidative lactonizations of meso-diols to give the corresponding lactones in up to 81% ee.

Asymmetric Catalytic Reduction of meso-Imides

A thiazazincolidine complex, 1, was shown to be an excellent catalyst for enantioselective reduction with bis(2,6-dimethylphenoxy)borane (BDMPB) of meso N-phenylimides in high ee to the corresponding hydroxy lactams, which were eventually converted to the corresponding lactones of high optical purity.

Highly Effective Diastereodifferentiation of Meso-Dicarboxylic Anhydrides Using Sterically Congested Chiral N-Sulfonylaminoalcohols

The differentiation between enantiotopic carbonyl groups of cyclic meso-dicarboxylic anhydrides has been attained with excellent diastereofacial selectivity with an isomer ratio above 99:1 by treatment with the lithium salts of sterically hindered chiral

Asymmetric Diels-Alder reaction of unsymmetrical maleates. A chemical access to chiral, unsymmetrical cis-cyclohexene-1,2-dicarboxylates

A new route to optically active, unsymmetrical cis-cyclohexene-1,2-dicarboxylate derivatives has been developed on the basis of the asymmetric Diels-Alder reaction of chiral, unsymmetrical maleates catalyzed by certain Lewis acids. A notably high level of asymmetric induction has been observed in the asymmetric Diels-Alder reaction of unsymmetrical maleates possessing chiral auxiliaries such as α-phenethyl and trans-2-phenylcyclohexyl groups. The origin of the chiral outcome using these dienophiles has been elucidated.

Enantioselective reduction of meso-cyclic-1,2-dicarboxylic anhydrides and 1,2-dicarboximides: Asymmetric synthesis of bicyclic lactones and hydroxylactams

Chiral bicyclic lactones (3,8,9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1,2- dicarboxylic anhydrides (1, 4) and meso-cyclic-1,2-dicarboximides (2) with lithium aluminum hydride (LiAlH4)-alcohol(ROH)-(R)- or (S)-1,1'-bi-2- naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave chiral bicyclic lactams (14, 15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14, 15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16, 17) in high optical purity.

Highly enantioselective reduction of meso-1,2-dicarboxylic anhydrides

Optically active lactones (2a-2g) were synthesized by highly enantioselective reduction of readily available meso-1,2-dicarboxylic anhydrides (1a-1g) using lithium aluminum hydride-ethanol-1,1'-bi-2-naphthol complex (BINAL-H).

Synthesis and Asymmetric Diels-Alder Reaction of Dimethyl ('d-Isoborneol-10-sulphinyl')maleate: Novel Route to Key Intermediates for Synthesis of Some Carbocyclic Nucleosides and Terpenoids

The chiral sulphoxide 1 was synthesized from 10-mercaptoisoborneol via diastereoselective oxidation.The dienophile 1 reacted with cyclopentadiene in the presence of a Lewis acid to give the adducts 7 and 8 with high diastereoselectivity (ca. 100percent).D

An Enantiodivergent Synthesis of Fused Bicycloheptane Lactones via an Asymmetric Diels-Alder Reaction

An enantiodivergent synthesis of the bicycloheptane lactone (2) is described, by regioselective reduction of the Diels-Alder adducts (3) and (4) with di-isobutylaluminium hydride followed by reductive elimination of the chiral auxiliary, 10-mercaptoisoborneol (9) through reaction with samarium(II) iodide.

PREPARATION OF ENANTIOMERICALLY PURE 3-ENDO-SULFONYLMETHYL SUBSTITUTED BICYCLOHEPTANE-2-ENDO-CARBOXYLIC ACIDS

Both enantiomers of title acids 5 were synthesized from mono-ester rac-1.An alternative approach via PLE catalyzed hydrolysis of a meso diester is described too.

Enantiodivergent Route to Both Enantiomers of β-Santalene and epi-β-Santalene from a Single Chiral Template

An enantiodivergent route to both enantiomers of β-santalene, constituents of East Indian sandalwood oil, has been developed using a single chiral template.