105970-10-3

Upstream product

• 21473-01-8 2-naphthalenylmagnesium bromide 
• 89-82-7 pulegone 

Downstream Products

• 105970-13-6 (1R,2S,5R)-8-(β-naphthyl)menthol 
• 105970-14-7 (1S,2S,5R)-5-Methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexanol 
• 105970-13-6 8-(2-naphthyl)menthol 
• 183434-73-3 Trifluoro-methanesulfonic acid (3R,6S)-3-methyl-6-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohex-1-enyl ester 
• 183434-74-4 (1R,2R,5R)-5-Methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexanecarboxylic acid methyl ester 
• 183434-78-8 2-{1-Methyl-1-[(1R,2S,4R)-4-methyl-2-((1Z,4Z)-6-methyl-hepta-1,4-dienyl)-cyclohexyl]-ethyl}-naphthalene 
• 183434-77-7 (1R,2R,5R)-5-Methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexanecarbaldehyde 
• 183434-76-6 [(1R,2R,5R)-5-Methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl]-methanol 
• 322640-63-1 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 322640-52-8 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 152481-93-1 (1R,2S,5R)-(+)-2-(1-methyl-1-β-naphthylethyl)-5-methylcyclohexyl dichloroacetate 

Relevant academic research and scientific papers

Chiral auxiliaries for asymmetric radical cyclization reactions: application to the enantioselective synthesis of (+)-triptocallol.

[figure: see text] A series of epimeric 8-aryl menthyl derivatives 5a-d and 6a-l, prepared from the same chiral source (R)-pulegone, were employed as chiral auxiliaries in the asymmetric radical cyclization reactions of beta-keto esters mediated by Mn(OAc)3. Chiral precursors 8c and 8d provided the cyclization products 10c and 10d, respectively, as single isomers (dr > 99:1), whereas the cyclization of precursor 9k gave 13k with good stereoselectivity (dr = 24:1). Diastereomer 13e was employed as the key intermediate in the enantioselective synthesis of (+)-triptocallol in 90% ee.

Auxiliary-directed peroxidation of 1,4-dienes

The addition of singlet oxygen (1O2) to the proximal alkene of auxiliary-tethered 1,4-dienes and the addition of triplet oxygen 3O2) to the proximal position of the corresponding pentadienyl radicals both produce conjugated diene hydroperoxides in moderate to high diastereomeric excess. Negligible stereoselection is observed for additions of 1O2 to the distal alkene of Z,Z-heptadienes due to the lack of control of alkene conformation. Despite evidence for the intermediacy of highly constrained pentadienyl radicals, poor diastereoselection is also observed for distal addition of 3O2. The extent of olefin isomerization observed during radical oxygenations can be correlated with steric constraints on the intermediate pentadienyl and peroxyl radicals and may be relevant to literature reports of olefin isomerization during enzymatic oxygenations of unnatural fatty acids.

SYNTHESIS OF THIOALDEHYDES HAVING OPTICALLY ACTIVE ALKOXY MOIETY AND THEIR ASYMMETRIC HETERO DIELS-ALDER REACTION

Optically active α-alkoxycarbonylthioaldehydes (2a-g) were prepared using 8-arylmenthols as chiral auxiliaries.Their asymmetric hetero Diels-Alder reactions with cyclopentadiene gave the endo cycloadducts (3 and 4) and exo cycloadducts (5 and 6) with moderate diastereomeric excesses.However, the major endo cycloadducts (3b-g) were isolated in optically pure form.This is the first chiral synthesis of 2-thiabicyclohept-5-ene ring system.The absolute configuration of the cyclic carbonate (12), which was prepared from the major endo cycloadduct (3c) via the epimerization, or the minor exo compound (6c), was determined as 1R by X-ray analysis.The cycloadduct (3c) was trasformed to a potential intermediate (14) for the synthesis of carbocyclic homonucleosides.

Improved Asymmetric Synthesis of 8-Arylmenthols

A two-step synthesis of a set of arylmenthones 3 from R(+)-pulegone 2 via their silylenoethers 4 is proposed leading in high yields to 8-arylmenthols 1.