145198-95-4

Upstream product

• 4083-64-1 Tosyl isocyanate 
• 145198-83-0 4-Phenyl-6-vinyl-[1,3]dioxan-2-one 
• 102632-99-5 1-phenyl-4-penten-1-ol 
• 61201-27-2 1-phenylpenta-4,5-dien-1-ol 
• 4009-55-6 penta-3,4-dienal 
• 30332-99-1 penta-3,4-dienoic acid ethyl ester 
• 145198-95-4 cis-N-(p-Toluenesulfonyl)-3-phenyl-5-vinyl-6-aza-2-oxacyclohexan-1-one 
• 108-86-1 bromobenzene 

Downstream Products

• 145198-95-4 trans-N-(p-Toluenesulfonyl)-3-phenyl-5-vinyl-6-aza-2-oxacyclohexan-1-one 

Relevant academic research and scientific papers

Rhodium-Catalyzed Diastereoselective Cyclization of Allenyl-Sulfonylcarbamates: A Stereodivergent Approach to 1,3-Aminoalcohol Derivatives

A diastereoselective and stereodivergent rhodium-catalyzed intramolecular coupling of sulfonylcarbamates with terminal allenes is described and it provides selective access to 1,3-aminoalcohol derivatives, scaffolds found in bioactive compounds. The reaction is compatible with a large range of different functional groups, thus furnishing products with high diastereoselectivities and yields. Moreover, multigram scale reactions, as well as the application of suitable product transformations were demonstrated.

Synthesis of anti-1,3 Amino Alcohol Motifs via Pd(II)/SOX Catalysis with the Capacity for Stereodivergence

We report the development of a Pd(II)/(±)-MeO-SOX/2,5-dimethylbenzoquinone system that enables unprecedented access to anti-1,3 amino alcohol motifs in good yields (33 substrates, avg. 66% isolated yield, >20:1 dr) and high selectivities (avg. 10:1 dr). Switching ligands to (±)-CF3-SOX with the use of a less bulky quinone oxidant, the kinetic syn-1,3 amino alcohol motif can be accessed in comparable yields and selectivities. Advantages of the stereodivergent nature of this reaction are seen in the synthesis of anti- and syn-1,3 amino alcohol vitamin D3 analogue intermediates in half the steps and higher overall yield relative to previous routes. Additionally, all eight possible stereoisomers of a chiral diamino alcohol core are generated from two amino acids. Mechanistic studies reveal that the anti-isomer is furnished through concurrent Pd(II)(SOX) catalyzed C-H amination and Pd(0)(SOX) catalyzed isomerization cycles.

A stereoselective approach to 1,3-amino alcohols protected as cyclic carbamates: Kinetic vs. thermodynamic control

Direct enantiocontrolled access to 1,3-amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama-aldol addition)

Regio- and stereoselective synthesis of 1,3-hydroxyl amines via palladium-catalyzed carbonate-carbamate transformation with unique stereoselectivity: Synthesis of 3-amino-4-penten-1-ols

The transformation of cyclic carbonates 1 to cyclic carbamates 4 is achieved in the presence of aryl or sulfonyl isocyanate by the catalysis of Pd(0) in high yield and with high structural flexibility. The reaction shows unique stereoselectivity: 3,4-disubstituted carbonates 2, irrespective of the composition of their stereoisomers, provide trans-5 exclusively or predominantly over cis-5. Mixtures of cis- and trans-3,5-disubstituted carbonates 3 furnish either cis-6 or trans-6 in high selectivity depending on the reaction conditions (kinetic or thermodynamic control, respectively). 1H NMR and X-ray structure analyses of 5 and 6 indicate that the stereochemical outcome is governed by an A1,2-strain between N-sulfonyl and C5-vinyl substituents.

Palladium-catalysed Regio- and Stereo-selective Synthesis of Allylic Amines

3-Vinyl-2,6-dioxacyclohexan-1-ones 1, by treatment with N-tosyl or N-arylisocyanates and a catalytic amount of Pd0, are converted into N-tosyl- and N-aryl-3-vinyl-2-aza-6-oxacyclohexan-1-ones 2 in good yields and with unique stereoselectivity.