Enantioselective synthesis induced by chiral organic-inorganic hybrid silsesquioxane in conjunction with asymmetric autocatalysis

Tetrahedron Letters

Volumn 45, Issue 42, 2004, Pages 7939-7941

  Kawasaki, Tsuneomi ^a   Ishikawa, Keisuke ^a   Sekibata, Hiromitsu ^a   Sato, Itaru ^a   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Asymmetric autocatalysis; Asymmetric induction; Asymmetric synthesis; Chiral hybrid silsesquioxane

Indexed keywords

INORGANIC COMPOUND; ORGANIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 4644363386     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.135     Document Type: Article

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44. 2O (7.5 mL) and 3 M aq NaOH (50 μL) was added, the reaction mixture was refluxed for 6 d. The resulting colourless solid was filtered and washed successively with water, EtOH and acetone. After drying at 110°C for 6 h, white powder (R,R)-3b (410 mg, 92%) and (R,R)-3c (507 mg, quant.) were obtained, respectively. (R,R)-3b: IR (KBr): ν = 1562, 1651, 3351, (S,S)-3b: IR (KBr): ν = 1562, 1651, 3359. (R,R)-3c: IR (KBr): ν = 1558, 1647, 3336, (S,S)-3c: IR (KBr): ν = 1566, 1651, 3332
45. 2Zn to pyrimidine-5-carbaldehyde 1 to afford (R)-pyrimidyl alkanol 2 with 80-95% ee in 75-85% yield, while (S,S)-4 gave (S)-2 with 80-92% ee in 81-86% yield