637337-60-1

Upstream product

• 94471-35-9 benzyl N-(methoxymethyl) carbamate 
• 637337-44-1 (4R)-3-(6-bromo-1-oxohexyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 1220596-99-5 benzyl N-[(benzyloxy)methyl]carbamate 
• 191090-32-1 (R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one 
• 22809-37-6 6-bromohexanoyl chloride 

Downstream Products

• 637337-17-8 (4R)-3-[(2S)-6-azido-2-({[(benzyloxy)carbonyl]amino}methyl)-1-oxohexyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 

Relevant academic research and scientific papers

Benzyl N-[(benzyloxy)methyl]carbamate: An improved aminomethylation electrophile for the synthesis of (benzyloxy)carbonyl (Cbz)-protected chiral β2-amino acids

α-Aminomethylation of (R)-DIOZ-alkylated (DIOZ=4-isopropyl-5,5- diphenyloxazolidin-2-one) substrates is a key step in the asymmetric synthesis of β2-amino acids, but it is unfortunately often accompanied by formation of transcarbamation by-prod

Preparation of β2-amino acid derivatives (β2hThr, β2hTrp, β2hMet, β2hPro, β2hLys, pyrrolidine-3-carboxylic acid) by using DIOZ as chiral auxiliary

The title compounds were prepared from valine-derived N-acylated oxazolidin-2-ones, 1-3, 7, 9, by highly diastereoselective (≥ 90%) Mannich reaction (→ 4-6; Scheme 1) or aldol addition (→ 8 and 10; Scheme 2) of the corresponding Ti- or B-enolates as the key step. The superiority of the '5,5-diphenyl-4-isopropyl-1,3-oxazolidin-2-one' (DIOZ) was demonstrated, once more, in these reactions and in subsequent transformations leading to various t-Bu-, Boc-, Fmoc-, and Cbz-protected β2-homoamino acid derivatives 11-23 (Schemes 3-6). The use of ω-bromo-acyl-oxazolidinones 1-3 as starting materials turned out to open access to a variety of enantiomerically pure trifunctional and cyclic carboxylic-acid derivatives.