64559-97-3

Upstream product

• 1056246-70-8 2-bromo-1-tetralone 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 447-53-0 1,2-Dihydronaphthalene 
• 119245-55-5 (2,3-Dihydro-1aH-1-oxa-cyclopropa[a]naphthalen-7b-yloxy)-trimethyl-silane 
• 41099-31-4 2-iodo-1-tetralone 
• 784179-06-2 phosphoric acid 3,4-dihydro-naphthalen-1-yl ester diethyl ester 
• 573-57-9 1,4-epoxy-1,4-dihydronaphthalene 
• 38858-72-9 1-trimethylsiloxy-3,4-dihydronaphthalene 
• 73611-99-1 2-Hydroxypropiophenone dimethylacetal 
• 1402704-92-0 C₁₈H₁₃NO₃ 
• 64245-04-1 2-bromo-1-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 19455-84-6 3,4-dihydronaphthalen-1-yl acetate 
• 134644-00-1 methyl 2-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 
• 18672-77-0 2-acetoxy-3,4-dihydronaphthalen-1(2H)-one 

Downstream Products

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 574-00-5 1,2-Dihydroxynaphthalene 
• 135-19-3 β-naphthol 
• 124718-65-6 2'(RS)-(1'-oxo-1',2',3',4'-tetrahydronaphthyl) 3,4,6-tri-O-benzyl-2-deoxy-2-(phenylthio)-β-D-glucopyranoside 
• 89920-57-0 (1S,2R)-cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 57496-61-4 (1R,2R)-trans-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 140134-31-2 (R)-(+)-2-hydroxy-3,4-dihydro-2H-naphthalen-1-one 
• 57495-92-8 (1R,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol 
• 182822-22-6 (2S)-1-oxo-2-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 14211-53-1 cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 14211-53-1 trans-naphthalene-1,2,3,4-tetrahydro-1,2-diol 

Relevant academic research and scientific papers

Enantioselective benzylation and allylation of α-trifluoromethoxy indanones under phase-transfer catalysis

The organo-catalyzed enantioselective benzylation reaction of α-trifluoromethoxy indanones afforded α-benzyl-α-trifluoromethoxy indanones with a tetrasubstituted stereogenic carbon center in excellent yield with moderate enantioselectivity (up to 57% ee). Cinchona alkaloid-based chiral phase transfer catalysts were found to be effective for this transformation, and both enantiomers of α-benzyl-α-trifluoromethoxy indanones were accessed, depended on the use of cinchonidine and cinchonine-derived catalyst. The method was extended to the enantioselective allylation reaction of α-trifluoromethoxy indanones to give the allylation products in moderate yield with good enantioselectivity (up to 76% ee).

Ir/Zn Dual Catalysis: Enantioselective and Diastereodivergent α-Allylation of Unprotected α-Hydroxy Indanones

A one-step enantioselective and diastereodivergent α-allylation of unprotected α-hydroxy indanones has been developed using an Ir/Zn dual catalyst system; no additional base is required. The cyclic tertiary α-hydroxyketones containing vicinal stereocenter

Catalytic Enantioselective Transannular Morita-Baylis-Hillman Reaction

Catalytic and enantioselective approaches to transannular reactions are very limited and mostly are based on chiral Lewis acid catalyzed pericyclic reactions. In this report, we present an efficient and straightforward methodology to access bicyclic carbo

Asymmetric Oxidation of Enol Derivatives to α-Alkoxy Carbonyls Using Iminium Salt Catalysts: A Synthetic and Computational Study

We report herein the first examples of asymmetric oxidation of enol ether and ester substrates using iminium salt organocatalysis, affording moderate to excellent enantioselectivities of up to 98% ee for tetralone-derived substrates in the α-hydroxyketone products. A comprehensive density functional theory study was undertaken to interpret the competing diastereoisomeric transition states in this example in order to identify the origins of enantioselectivity. The calculations, performed at the B3LYP/6-31G(D) level of theory, gave good agreement with the experimental results, in terms of the magnitude of the effects under the specified reaction conditions, and in terms of the preferential formation of the (R)-enantiomer. Just one of the 30 characterized transition states dominates the enantioselectivity, which is attributed to the adoption of an orientation relative to stereochemical features of the chiral controlling element that combines a CH interaction between a CH2 group in the substrate and one of the aromatic rings of the biaryl section of the chiral auxiliary with a good alignment of the acetoxy group with the other biaryl ring, and places the smallest substituent on the alkene (a hydrogen atom) in the most sterically hindered position.

Divergent synthesis of N-heterocycles by Pd-catalyzed controllable cyclization of vinylethylene carbonates

Here, we report a palladium-catalyzed controllable cyclization of vinyl ethylene carbonates that proceeds through formal migration [2+3] and [5+2] cycloadditions, respectively, under mild conditions. The transformation described here affords a series of synthetically versatile 5,7-membered N-heterocycles which are found in natural products and pharmaceuticals with biological and medicinal properties.

Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C?N/C?S Bond Formation in Allylic Surrogates

Switchable catalytic transformation of reactants can be a powerful approach towards diversity-orientated synthesis from easily available molecular synthons. Herein, an endogenous ligand-controlled, Pd-catalyzed allylic substitution allowing for either selective C?N or C?S bond formation using vinylethylene carbonates (VECs) and N-sulfonylhydrazones as coupling partners has been developed. This versatile methodology provides a facile, divergent route for the highly chemo- and stereoselective synthesis of functional allylic sulfones or sulfonohydrazides. The newly developed protocol features wide substrate scope (nearly 80 examples), broad functional group tolerance, and potential for the late-stage functionalization of bioactive compounds. The isolation and crystallographic analysis of a catalytically competent π-allyl Pd complex suggests that the pathway leading to the allylic products proceeds through a different manifold as previously proposed for the functionalization of VECs with nucleophiles.

Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides

A common approach to the synthesis of α-oxygenated carbonyl compounds and catechols is the treatment of a carbonyl compound or a phenol with an electrophilic oxygen source. As an alternative approach to these important structures, formal [3,3]-rearrangements of N-enoxyphthalimides, N-enoxyisoindolinones, and N-aryloxyphthalimides have been explored. When used in combination with an initial Chan-Lam coupling, these transformations facilitate the dioxygenation of alkenylboronic acids for the synthesis of α-oxygenated ketones and the dioxygenation of arylboronic acids for the synthesis of catechols. The rearrangements of N-enoxyisoindolinones have also been shown to be diastereoselective.

Highly enantioselective hydrogenation of o-alkoxy tetrasubstituted enamides catalyzed by a Rh/(R, S)-josiphos catalyst

Rh/(R,S)-JosiPhos complex-catalyzed asymmetric hydrogenation of o-alkoxy tetrasubstituted enamides has been achieved, and it furnished a set of β-amino alcohol analogues in high yields and excellent enantiomeric excesses (>99% conversion, up to 99% ee).This method provides valuable chiral building blocks in chiral pharmaceuticals and useful motifs for catalysts.

Flexible stereoselective functionalizations of ketones through umpolung with hypervalent iodine reagents

The functionalization of carbonyl compounds in the α-position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or "umpolung", we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel retrosynthetic planning and rapid assembly of structures previously accessible only by multistep sequences. A Nu approach: An efficient α-functionalization of ketones with a range of simple and useful nucleophiles is possible by using hypervalent iodine reagents (see scheme; Nu′ can be the Nu itself or a protected form of this nucleophile group).

Preparation of α-oxygenated ketones by the dioxygenation of alkenyl boronic acids

Two in two: Dioxygenation of alkenyl boronic acids has been achieved with N-hydroxyphthalimide. The two-step process involves etherification of an alkenyl boronic acid with N-hydroxyphthalimide followed by a [3,3] rearrangement. The dioxygenated product can then be hydrolyzed to form either the corresponding α-hydroxy ketone or the α-benzoyloxy ketone. Copyright