271260-90-3

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 117833-92-8 (4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde 
• 186759-45-5 (+/-)-(1-hydroxymethallyl)carbamic acid benzyl ester 
• 31139-36-3 dibenzyl dicarbonate 
• 91103-38-7 (R)-(1-hydroxymethallyl)carbamic acid benzyl ester 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 271261-12-2 (R)-2-(benzyloxycarbonyl)amino-4-(4-chloropyridin-2-yl)-1-butanol 
• 271261-13-3 (R)-2-(benzyloxycarbonyl)amino-4-(4-methoxyphenyl)-1-butanol 
• 271261-17-7 (R)-2-[(benzyloxycarbonyl)amino]-4-(2-isopropyl-5-methylphenyl)-1-butanol 
• 444993-34-4 (R)-4-[(E)-2-(4-Methoxy-phenyl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 412917-37-4 benzyl (4R)-2,2-dimethyl-4-[2-(4-methoxyphenyl)ethyl]-1,3-oxazolidine-3-carboxylate 
• 412917-38-5 benzyl (4R)-2,2-dimethyl-4-[2-(2-nitrophenyl)ethyl]-1,3-oxazolidine-3-carboxylate 
• 1258210-40-0 S-(-)-benzyl 4-acetyl-2,2-dimethyoloxazolidine-3-carboxylate 

Relevant academic research and scientific papers

Catalyst-controlled Wacker-type oxidation of protected allylic amines

On the contrary: Utilizing the [Pd-(quinox)]-TBHP catalyst system, protected allylic amines were oxidized with high selectivity for the methyl ketone product. This is contrary to the results obtained by the substrate-controlled Tsuji-Wacker oxidation, which highlights the catalyst-controlled system presented here (see scheme). A variety of N-pro-tecting groups undergo selective oxidation with high ketone selectivity. TBHP = tert-butylhydroperoxide.

Enantiomerically pure α-amino acid synthesis via hydroboration - Suzuki cross-coupling

The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis -oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.

Synthesis of unnatural amino acids via suzuki cross-coupling of enantiopure vinyloxazolidine derivatives

(R and S)-α-Amino alcohols and α-amino acids, including 4-methoxyhomophenylalanine, with a variety of unnatural side chains have been synthesized via palladium-catalyzed cross-coupling Suzuki reactions. The key building blocks 1 and 2, synthesized from the common achiral precursor 2-butene-1,4-diol, were made enantiopure utilizing a Pseudomonas cepacia lipase-catalyzed kinetic resolution. The optimal conditions for the Suzuki cross-coupling and the subsequent oxidations of the resultant α-amino alcohols are described.