223906-38-5

Usage

InChI:InChI=1/C8H15NO2/c1-5(2)6-8(3,4)11-7(10)9-6/h5-6H,1-4H3,(H,9,10)/t6-/m1/s1

Upstream product

• 223906-58-9 (4R)-N-<(2S)-2-Methyl-1-oxo-3-phenylpropyl>-5,5-dimethyl-4-isopropyloxazolidin-2-one 
• 1396008-61-9 (R)-3-(2-phenylacryloyl)-4-isopropyl-5,5-dimethyloxazolidin-2-one 
• 1396008-63-1 (4R)-3-[(2S)-2-phenyl-3-(N-benzylamino)propanoyl]-4-isopropyl-5,5-dimethyloxazolidin-2-one 
• 1396008-67-5 C₄₀H₆₁N₃O₅ 
• 1396008-62-0 (4R)-3-[(2S)-2-phenyl-3-(N,N-dibenzylamino)propanoyl]-4-isopropyl-5,5-dimethyloxazolidin-2-one 

Downstream Products

• 223906-58-9 (4R)-N-<(2S)-2-Methyl-1-oxo-3-phenylpropyl>-5,5-dimethyl-4-isopropyloxazolidin-2-one 
• 1396008-61-9 (R)-3-(2-phenylacryloyl)-4-isopropyl-5,5-dimethyloxazolidin-2-one 
• 1396008-62-0 (4R)-3-[(2S)-2-phenyl-3-(N,N-dibenzylamino)propanoyl]-4-isopropyl-5,5-dimethyloxazolidin-2-one 
• 1396008-66-4 (4R)-3-[(2R)-2-phenyl-3-(N,N-dibenzylamino)propanoyl]-4-isopropyl-5,5-dimethyloxazolidin-2-one 
• 1396008-63-1 (4R)-3-[(2S)-2-phenyl-3-(N-benzylamino)propanoyl]-4-isopropyl-5,5-dimethyloxazolidin-2-one 
• 1396008-65-3 (4R)-3-{(2S)-2-phenyl-3-[N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one 
• 1396008-67-5 C₄₀H₆₁N₃O₅ 
• 1396008-68-6 (4R)-3-[(2R)-2-phenyl-3-(N-benzylamino)propanoyl]-4-isopropyl-5,5-dimethyloxazolidin-2-one 

Relevant academic research and scientific papers

Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C

The first asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C is described. This synthesis employs the conjugate addition of lithium dibenzylamide to an N-α-phenylacryloyl SuperQuat derivative followed by diastereoselective protonation of the intermediate enolate using 2-pyridone as the key step to introduce the stereochemistry. (-)-(S)-Nakinadine C was isolated in 13% yield over 9 steps from commercially available atropic acid, 98:2 dr [(Z):(E) ratio] and >99% ee.

(-)-(S)-Nakinadine B: First asymmetric synthesis

(-)-(S)-Nakinadine B has been synthesized for the first time (in 9 steps and 17% overall yield from commercially available atropic acid) using the conjugate addition of lithium dibenzyl-amide to an N-α-phenylacryloyl SuperQuat derivative with in situ dias

Asymmetric alkylations using SuperQuat auxiliaries - An investigation into the synthesis and stability of enolates derived from 5,5-disubstituted oxazolidin-2-ones

Studies on the alkylation of enolates derived from a range of N-acyl-5,5-dimethyloxazolidin-2-ones and N-acyl-5,5-diphenyloxazolidin-2-ones reveal that high yields and high diastereoselectivities are best obtained when homochiral 4-isopropyl-5,5-dimethyloxazolidin-2-one is employed as a chiral auxiliary.