23204-71-9

Upstream product

• 1189-71-5 isocyanate de chlorosulfonyle 
• 1439-07-2 trans-Stilbene oxide 
• 530-36-9 threo-1,2-diphenyl-2-aminoethan-1-ol 
• 503-38-8 trichloromethyl chloroformate 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 801219-76-1 2-(diphenylphosphinamide)-1,2-diphenylethanone 
• 904922-22-1 4,5-dimethyl-2-(phenyl-trimethylsilanyloxy-methyl)-thiazole 
• 100-52-7 benzaldehyde 
• 98837-46-8 N-benzylidenediphenylphosphinamide 
• 5908-41-8 benzoyltrimethylsilane 
• 169899-58-5 2-(1-hydroxy-1-phenylmethyl)-4,5-dimethylthiazole 
• 163667-14-9 2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 591-51-5 phenyllithium 
• 146405-41-6 [2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethylidene]-trimethylsilanyl-amine 

Downstream Products

• 170080-05-4 (4S,5S)-4,5-diphenyl-2-oxazolidinone 
• 86286-50-2 (4R,5S)-4,5-diphenyl-1,3-oxazolidin-2-one 
• 139165-52-9 ((1R,2R)-2-Hydroxy-1,2-diphenyl-ethyl)-carbamic acid tert-butyl ester 
• 42746-66-7 3-nitroso-4r,5t-diphenyl-oxazolidin-2-one 
• 55041-24-2 3-amino-4r,5t-diphenyl-oxazolidin-2-one 

Relevant academic research and scientific papers

Alkene Syn- And Anti-Oxyamination with Malonoyl Peroxides

Malonoyl peroxide 6 is an effective reagent for the syn- or anti-oxyamination of alkenes. Reaction of 6 and an alkene in the presence of O-tert-butyl-N-tosylcarbamate (R3 = CO2 tBu) leads to the anti-oxyaminated product in up to 99% yield. Use of O-methyl-N-tosyl carbamate (R3 = CO2Me) as the nitrogen nucleophile followed by treatment of the product with trifluoroacetic acid leads to the syn-oxyaminated product in up to 77% yield. Mechanisms consistent with the observed selectivities are proposed.

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: Theoretical evidence for an asynchronous concerted pathway

The one-pot reaction of chlorosulfonyl isocyanate (CSI) with epoxides having phenyl, benzyl and fused cyclic alkyl groups in different solvents under mild reaction conditions without additives and catalysts was studied. Oxazolidinones and five-membered cyclic carbonates were obtained in ratios close to 1:1 in the cyclization reactions. The best yields of these compounds were obtained in dichloromethane (DCM). Together with 16 known compounds, two novel oxazolidinone derivatives and two novel cyclic carbonates were synthesized with an efficient and straightforward method. Compared to the existing methods, the synthetic approach presented here provides the following distinct advantageous: being a one-pot reaction with metal-free reagent, having shorter reaction times, good yields and a very simple purification method. Moreover, using the density functional theory (DFT) method at the M06-2X/6-31+G(d,p) level of theory the mechanism of the cycloaddition reactions has been elucidated. The further investigation of the potential energy surfaces associated with two possible channels leading to oxazolidinones and five-membered cyclic carbonates disclosed that the cycloaddition reaction proceeds via an asynchronous concerted mechanism in gas phase and in DCM.

Catalytic, enantioselective N-acylation of lactams and thiolactams using amidine-based catalysts

In contrast to alcohols and amines, racemic lactams and thiolactams cannot be resolved directly via enzymatic acylation or classical resolution. Asymmetric N-acylation promoted by amidine-based catalysts, particularly Cl-PIQ 2 and BTM 3, provides a convenient method for the kinetic resolution of these valuable compounds and often achieves excellent levels of enantioselectivity in this process. Density functional theory calculations indicate that the reaction occurs via N-acylation of the lactim tautomer and that cation-π interactions play a key role in the chiral recognition of lactam substrates.

Synthesis and configurational assignment of the amino alcohol in the eastern fragment of the GE2270 antibiotics by regio- and stereoselective addition of 2-metalated 4-bromothiazoles to α-chiral electrophiles

A synthesis of the eastern fragment of the thiazole peptide GE2270 A (1) has been developed. The synthetic approach relies on the regioselective functionalization of 2,4-dibromothiazole (5) via metalation and nucleophilic addition (at C2) or palladium-mediated cross-coupling (at C2 or C4). The stereochemistry at the N-bearing stereocenter was established by coupling of 2-metalated 4-bromothiazoles (4) to enantiomerically pure mandelic acid derivatives. Both the erythro (2) and threo (3) configurated amino alcohols were prepared with high diastereoselectivities depending on the electrophile employed. More specifically, the threo-configurated (S,R)-4-bromothiazolyl β-amino alcohol 6 was synthesized from O-TBS protected (R)-mandelonitrile in 62% yield. Its N-PMB protected (R,S)-enantiomer 20 was obtained from O-TBS protected (S)-mandelic aldehyde in 67% yield. The eryrthro-configurated (S,S)-4-bromothiazolyl β-amino alcohol 29 was prepared from O-TBS protected (S)-ethyl mandelate in four steps and 33% overall yield. The bithiazole moiety in the desired products 2 and 3 was finally established by the regioselective Negishi coupling of 2,4-dibromothiazole (5) and the 4-zincated, N-Boc protected thiazole derivatives of the diastereomeric 4-bromothiazolyl β-amino alcohols 6 and 29.

Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation

Kinetic resolution of racemic 2-oxazolidinones via catalytic, enantioselective N-acylation has been achieved for the first time and with outstanding selectivities. Copyright

Catalytic additions of acylsilanes to imines: An acyl anion strategy for the direct synthesis of α-amino ketones

(Chemical Equation Presented) The addition of acylsilanes to imines catalyzed by neutral carbenes (or zwitterions) generated in situ from readily available thiazolium salts is described. The general reaction successfully utilizes acylsilanes as carbonyl anion precursors and is tolerant of a range of structural diversity on the acylsilane or imine electrophile. The overall reaction utilizes easily available precursors and directly accesses protected α-amino ketones in the correct oxidation state.

Chemoselective debezylation of the N-1-phenylethyl group in 2-oxazolidinones by the anisole-methanesulfonic acid system

The chemoselective removal of N-1-phenylethyl group in 2-oxazolidinones by the anisole-methanesulfonic acid system was investigated. Optically active 4,5-cis- and 4,5-trans-diphenyl-2-oxazolidinones (1a-d) were easily synthesized from dl-stilbene oxides (trans- and cis-7a) using this debenzylation.

Facile inversion of configuration of N-Boc-β-aminoalcohols via S(N)2 cyclization to oxazolidinones

Oxazolidinones are obtained by the cyclization of mesylates derived from N-Boc-β-Aminoalcohols. Hydrolysis of the N-Boc-Oxazolidinones regenerates the protected aminoalcohols with inverted configuration at the hydroxy group. (C) 2000 Elsevier Science Ltd.

Practical modifications and applications of the sharpless asymmetric aminohydroxylation in the one-pot preparation of chiral oxazolidin-2-ones

Chiral oxazolidin-2-ones are synthetically valuable as chiral auxiliaries, and many have pharmaceutically interesting biological activity. This communication focuses on a convenient, practical one-pot preparation of chiral 4,5-disubstituted oxazolidan-2-o