81658-24-4

Upstream product

• 17199-29-0 (S)-Mandelic acid 
• 21210-43-5 (S)-Methyl mandelate 
• 169220-96-6 (S)-methoxymethoxy-phenyl-acetic acid methyl ester 
• 124-38-9 carbon dioxide 
• 113249-00-6 {α-{(methoxymethyl)oxy}benzyl}tributylstannane 

Downstream Products

• 81658-23-3 5-((S)-Methoxymethoxy-phenyl-methyl)-oxazole-4-carboxylic acid methyl ester 
• 1357157-30-2 N-(2-bromophenyl)-2-hydroxy-N-methyl-2-phenylacetamide 
• 1335113-49-9 (S)-N-(2-bromophenyl)-2-(methoxymethoxy)-N-methyl-2-phenylacetamide 
• 81327-36-8 5-(Methoxymethoxy-phenyl-methyl)-oxazole-4-carboxylic acid methyl ester 
• 161109-20-2 methyl 2-(methoxymethoxy)-2-phenylethanoate 
• 81378-00-9 N-(4-Hydroxy-2-oxo-5-phenyl-2,5-dihydro-furan-3-yl)-acetamide 
• 343945-84-6 3-Amino-4-hydroxy-5-phenyl-5H-furan-2-one 

Relevant academic research and scientific papers

Synthesis of arylglycine and mandelic acid derivatives through carboxylations of α-amido and α-acetoxy stannanes with carbon dioxide

Incorporation reactions of carbon dioxide (CO2) with N-Boc-α-amido and α-acetoxy stannanes were developed using CsF as a mild tin activator. Monoprotected α-amido stannanes could be used, and the corresponding arylglycine derivatives were obtained in moderate-to-high yields under 1 MPa (10 atm) of CO2 pressure. α-Acetoxy stannanes also underwent carboxylation to afford mandelic acid derivatives in excellent yields under ambient CO2 pressure. Both transformations enabled the synthesis of α-tertiary and α-quaternary carboxylic acid derivatives. In addition, the chirality of (S)-N-tert-butylsulfonyl-α- amido stannanes was transferred with up to 90% inversion of configuration at 100 °C.

The preparation of 2H-1,4-benzoxazin-3-(4H)-ones via palladium-catalyzed intramolecular C-O bond formation

Pd/PtBu3-catalyzed intramolecular C-O bond formation has been used to access aryl- and alkyl-substituted benzoxazinones.