66405-16-1

Upstream product

• 4373-13-1 4-methyl-1,2-dihydronaphthalene 
• 39202-04-5 1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol 
• 113388-93-5 1-Methyl-3,4-dihydro-naphthalene-2-carbaldehyde 
• 200425-59-8 (S)-(+)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 

Downstream Products

• 112818-02-7 3-(2-acetylphenyl)propionic acid ethyl ester 

Relevant academic research and scientific papers

Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters

Lactams with a stereogenic center adjacent to the N atom have existed in many medicinal agents and bioactive alkaloids. Herein we report a broadly applicable synthesis of enantioenriched NH lactams through a one-pot asymmetric reductive amination/cyclization sequence of easily available keto acids/esters. Such cascade processes alleviate the demand for protecting group manipulations as well as intermediate purification. This strategy is capable of constructing enantioenriched lactams and benzo-lactams of a five-, six-, or seven-membered ring in generally high yield and with excellent enantioselectivities (up to 97% ee). Scalable and concise syntheses of key drug intermediates have further displayed the importance of this methodology.

Synthesis of β-acetoxy alcohols by PhI(OAc)2-mediated metal-free diastereoselective β-acetoxylation of alcohols

β-Acetoxy alcohols can be synthesized in good yields with excellent diastereoselectivity from tertiary alcohols through PhI(OAc)2-mediated metal-free β-acetoxylation. Mechanistic studies showed that the β-acetoxylation process might undergo dehydration and sequential highly regioselective and diastereoseletive dioxygenation. Gram scale and diverse useful scaffolds could be prepared via this β-acetoxylation process.

REACTION OF α,β-UNSATURATED ALDEHYDES WITH HYDROGEN PEROXIDE CATALYSED BY BENZENESELENINIC ACIDS AND THEIR PRECURSORS

Oxidation of α,β-unsaturated aldehydes with hydrogen perixide catalysed by benzeneselenic acids and their precursors has been investigated.Bis 2-nitrophenyl diselenide has proved to be the most effective catalyst.The major products resulting from the oxidation are vinyl formates (a) which on hydrolysis give saturated aldehydes or ketones (g) having the carbon chain shortened by one carbon atom, compared with the starting aldehydes.The minor products are formyloxyoxiranes (b), α-hydroxycarbonyl (e) and α-formyloxycarbonyl (f) compounds with the carbon chain shortened by one carbon atom.Carbonyl compounds d, formally derived from an oxidative fission of the carbon-carbon double bond, have been also isolated.Diformyloxy (4c) and formyloxyacetoxy phenylmethane (5c) have been isolated when cinnamaldehyde (4) or 1-phenyl-2-formyloxypropane (5a) were oxidized, respectively.Possible mechanisms of formation of these products are discussed.Similar products resulted when α,β-unsaturated aldehydes were oxidized with organic peroxy acids.

ORTHO-SUBSTITUTED PHENYLPROPIONIC ACIDS. PART I. CYCLIZATION OF SOME 2-ACYLPHENYLPROPIONIC ACIDS TO HOMOISOCHROMAN DERIVATIVES

Some homoisochroman derivatives from the corresponding 2-(phenylhydroxymethyl)phenylpropanols were obtained.The latter compounds were prepared from 2-acylphenylpropionic acids.