72659-59-7

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 67-64-1 acetone 
• 87861-38-9 (R)-N-isopropyl-α-methylbenzylamine 

Downstream Products

• 1293306-05-4 C₂₉H₄₁NO₂Si₂ 
• 1293306-08-7 (3S,3aS,7S,7aR)-3-phenyl-7-(trimethylsilyl)hexahydro-1H-isoindole-1,5(6H)-dione 
• 1293305-94-8 tert-butyl (1S,3aR,4S,7aS)-3,6-dioxo-1-phenyl-4-(trimethylsilyl)hexahydro-1H-isoindole-2(3H)-carboxylate 
• 1293305-93-7 (3S,3aS,7S,7aR)-3-phenyl-2-(2-phenylpropan-2-yl)-7-(trimethylsilyl)hexahydro-1H-isoindole-1,5(6H)-dione 
• 414871-53-7 (3S,3aS,7aR)-2-(1-methyl-1-phenylethyl)-3-phenyl-2,3,3a,7a-tetrahydro-1H-isoindole-1,5(4H)-dione 

Relevant academic research and scientific papers

Enantioselective opening of spiro epoxides derived from cis bicyclo[3.3.0]octan-3,7-dione using chiral lithium amide bases

The monoketal derived from cis-bicyclo[3.3.0]octane-3,7-dione was converted to epoxides 3. Meso exo epoxide was cleaved via enantioselective deprotonaiton using chiral lithium amide bases to provide the synthetically useful alcohol 7 with up to 76%ee. The enantiomeric excess of the alcohol was determined by 1H NMR chiral shift techniques.

ENANTIOSELECTIVE DEPROTONATION OF THE MONOACETALS OF BICYCLOOCTAN-3,7-DIONE. AN APPROACH TO THE ASYMMETRIC SYNTHESIS OF CHIRAL SYNTHONS FOR CARBACYCLINS

Kinetic deprotonation of the monoacetals (4) of bicyclooctan-3,7-dione by chiral lithium amides (5) in the presence of excess trimethylsilyl chloride afforded the corresponding silyl enol ethers (6), useful synthons for the synthesis of optically active carbacyclins, in up to 94percent ee.