93667-62-0

Upstream product

• 97186-53-3 (Z)-1-benzyloxy-4-trichloroacetimidoxybut-2-ene 
• 81028-03-7 (Z)-4-benzyloxy-but-2-en-1-ol 
• 80885-30-9 (E)-4-(benzyloxy)-2-buten-1-ol 
• 69152-88-1 4-(benzyloxy)-2-buten-1-ol 
• 104808-53-9 1-(1-imino-2,2,2-trichloroethoxy)-4-benzyloxy-2(E)-butene 

Downstream Products

• 15167-30-3 O-benzyl-N-trichloroacetyl-serine 
• 97186-57-7 (E)-4-benzyloxymethyl-5-iodomethyl-2-trichloromethyl-4,5-dihydro-1,3-oxazole 
• 97186-57-7 (Z)-4-benzyloxymethyl-5-iodomethyl-2-trichloromethyl-4,5-dihydro-1,3-oxazole 
• 99726-02-0 1-(benzyloxy)but-3-en-2-amine hydrochloride 

Relevant academic research and scientific papers

Stereoselective synthesis of imidazolidin-2-ones via Pd-catalyzed alkene carboamination. Scope and limitations

A method for the synthesis of imidazolidin-2-ones from N-allylureas and aryl or alkenyl bromides via Pd-catalyzed carboamination reactions is described. The N-allylurea precursors are prepared in one step from readily available allylic amines and isocyanates, and the Pd-catalyzed reactions effect the formation of a C-C bond, a C-N bond, and up to two stereocenters in a single step. Good diastereoselectivities are obtained for the conversion of substrates bearing allylic substituents to 4,5-disubstituted imidazolidin-2-ones, and excellent selectivity for the generation of products resulting from syn-addition across the alkene is observed when substrates derived from cyclic alkenes or E-1,2-disubstituted alkenes are employed. A brief discussion of reaction mechanism and product stereochemistry is presented.

Allyl, epoxy and glycosyl perfluoroimidates. One-pot preparation and reaction

The one-pot preparation of allyl, epoxy and glycosyl perfluoroimidates and their reaction are described. Volatile perfluoronitriles were generated from perfluoroamides with an 'activated' dimethyl sulfoxide (DMSO) species at -78°C. Allyl, epoxy and glycosyl perfluoroimidates were prepared in 44-92% yield following in situ nucleophilic addition of alcohol and sugar derivatives to nitriles. The obtained trifluoroacetimidates were more stable than the trichloro analogue and were easily purified by SiO2 column chromatography and/or distillation. The 3,3-sigmatropic rearrangement of allylic analogues, acid-catalyzed cyclization of the epoxy analogues and glycosylation of sugar analogues were studied comparing with their corresponding trichloroacetimidates. The trifluoroacetimidates were considerably less reactive than trichloroacetimidates due to their electron-withdrawing substituents on the imidate carbon.

A New Approach to (+/-)-2-Amino-2-deoxytetritol Derivatives

A new approach to the (+/-)-2-amino-2-deoxytetritol derivatives (1), (2) and (3) is described, starting either from the allylic trichloroacetimidate (5) or from the allylic trichloroacetamidate (11).The 4,5-dihydro-oxazole (6), obtained by iodocyclization

A New α-Amino Acid Synthesis via an Acetimidate Rearrangement

A new efficient synthesis of α-amino acids from allyl alcohol derivatives via an acetimidate rearrangement has been developed.