198147-93-2

Upstream product

• 99333-55-8 2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride 
• 160067-44-7 (2S)-2-(triisopropylsiloxy)-N-(trimethylsilyl)propanimine 
• 123882-32-6 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid 
• 135614-60-7 (2S)-2-(triisopropylsilyloxy)propionaldehyde 
• 163440-49-1 N-trimethylsilylimine of 2(S)-(triisopropylsilyloxy)lactaldehyde 

Downstream Products

• 200808-48-6 (2R,5R,6S)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-2-((S)-1-triisopropylsilanyloxy-ethyl)-[1,3]oxazinan-4-one 
• 295781-35-0 (4S)-3-{(3R,4S)-2-oxo-4-[(S)-1-(triisopropylsilyloxy)ethyl]-1-(trimethylsilyl)azetidine-3-yl}-4-phenyloxazolidin-2-one 
• 295781-34-9 (4S)-3-{(3S,4R)-2-oxo-4-[(S)-1-(triisopropylsilyloxy)ethyl]-1-(trimethylsilyl)azetidine-3-yl}-4-phenyloxazolidin-2-one 
• 200808-50-0 [(2R,5R,6S)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-oxo-2-((S)-1-triisopropylsilanyloxy-ethyl)-[1,3]oxazinan-5-yl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis of perhydroxazin-4-ones. Competitive Mukaiyama versus hetero Diels-Alder reaction in the cycloaddition of 2-aza-3-trimethylsilyloxy-1,3-butadiene and aldehydes

The reactions of 2-aza-3-trimethylsilyloxy-1,3-butadiene with carbonyl dienophiles are described. 2-Aza-1,3-butadienes participate as dienes in the [4+2] cycloaddition with aldehydes to afford perhydroxazin-4-ones in good yields. Experimental results, however, show that a Mukaiyama type two-step reaction must be taken into account. The cycloadducts obtained have proved to be useful intermediates in the synthesis of α-amino-β-hydroxy acids.

Stereochemical aspects of a two-step staudinger reaction - asymmetric synthesis of chiral azetidine-2-ones

Reaction of N-trialkylsilylimines with a variety of glycine-derived ketenes produced 1,3-azadienes, which in some cases have been isolated and characterised. A conrotatory ring closure of these compounds gave rise to the formation of the azetidine-2-ones, thus allowing a formal two-step Staudinger reaction. Exclusive trans diastereoselectivity was observed. A less stringent diastereofacial selectivity was obtained. A set of experiments has been performed in order to evaluate the influence of the structural parameters as well as reaction conditions. Ab initio studies at MP2/6-31G* and QCISD(T)/6- 311G** levels on model compounds provide a rationalization of the experimental results obtained. From the experimental as well as theoretical data it is clear that the presence of the silyl enol group in the intermediate azadiene is crucial in its stabilisation and plays a fundamental role in the conrotatory ring closure and, therefore, in the formation of the azetidine-2-one ring.

Solution phase library of perhydrooxazin-4-ones

A general approach to the solution phase parallel synthesis of perhydrooxazin-4-ones, which allows the preparation of milligram quantities of each individual member, is reported. An efficient purification method, using as 'Sequestration Enabling Reagent' (SER) aminomethylpolystyrene resin in the presence of trimethylorthoformate is also described.