142612-75-7

Upstream product

• 142612-59-7 N-phenylethyl-N-p-methoxyphenyl-α-methoxycarbonyl-α-diazoacetamide 
• 14803-72-6 methyl N-(4-methoxyphenyl)carbamate 
• 2405-59-6 N-(2-phenylethyl)-4-methoxyaniline 
• 103-63-9 1-phenyl-2-bromoethane 
• 142613-21-6 N-(4-Methoxy-phenyl)-N-phenethyl-malonamic acid methyl ester 

Relevant academic research and scientific papers

Enantioselective synthesis of 4-substituted 2-pyrrolidinones by site- selective C-H insertion of α-methoxycarbonyl-α-diazoacetanilides catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate]

Site- and enantioselective intramolecular C-H insertion of α- methoxycarbonyl-α-diazoacetamides has been achieved by exploiting a p- nitrophenyl group as the N-substituent and dirhodium(II) tetrakis[N- phthaloyl-(S)-tert-leucinate] as catalyst, leading to the formation of 4 substituted 2-pyrrolidinone derivatives of up to 82% ee. The efficiency of the present protocol has been verified well by a short-step synthesis of (R)- (-)-baclofen.

Dirhodium Tetraacetate Catalyzed Carbon-Hydrogen Insertion Reaction in N-Substituted α-Carbomethoxy-α-diazoacetanilides and Structural Analogues. Substituent and Conformational Effects

A series of acyclic α-carbomethoxy-α-diazoacetanilides with different N-substituents, 5a-k, was prepared and the rhodium(II) acetate catalyzed reaction studied.It was found that the rhodium carbenoid reaction with these compounds occurred only at the N-substituent; when the N-substituent is a propargyl group, rhodium carbenoid addition to the triple bond is favored, resulting, ultimately, in the formation of a bicyclic furan derivative 8.With an N-(tert-butyloxycarbonyl)methyl substituent, interception of the rhodium carbenoid by the ester carbonyl oxygen occurred preferentially to give, eventually, 1,4-oxazine derivatives 9 and 9'.For N'-alkyl substituents, rhodium carbenoid carbon-hydrogen (C-H) insertion into the alkyl group to give the 2-azetidinone and/or 2-pyrrolidinone derivatives was observed.The chemoselectivity of the rhodium carbenoid C-H insertion can be altered by the use of the α-acetyl and α-phenylsulfonyl substituents.In these cases, exclusive C-H insertion at the N-aryl moiety resulted to give 2(3H)-indolinone products.However, the α-substituent effect on the chemoselectivity of the insertion reaction is easily overridden by conformational effects about the amide N-C(O) bond as revealed by the insertion reaction of the conformationally rigid compounds 20a-c.The α-substituent effects are reestablished when conformational rigidity is removed, as exemplified by the rhodium carbenoid insertion reactions of compounds 29a, b.