Chemistry Letters

Aldol addition reaction of chiral acetylurea and a convenient synthesis of optically pure methyl. BETA.-alkyl-. BETA.-hydroxypropionate.

K Kishikawa, M Yamamoto, S Kohmoto, K Yamada

Index: Kishikawa, Keiki; Yamamoto, Makoto; Kohmoto, Shigeo; Yamada, Kazutoshi Chemistry Letters, 1989 , p. 787 - 790

Full Text: HTML

Citation Number: 8

Abstract

The aldol addition reaction of chiral acetylurea with aldehydes diastereoselectively gives β- alkyl-β-hydroxypropionyl-ureas (3 and 4) and the methanolysis of the adducts 3 and 4, separated perfectly by conventional column chromatography on silica gel, gives the corresponding optically pure methyl β-alkyl-β-hydroxypropionates.

Related Articles:

New chiral diphosphine ligands designed to have a narrow dihedral angle in the biaryl backbone

[Saito, Takao; Yokozawa, Tohru; Ishizaki, Takero; Moroi, Takashi; Sayo, Noboru; Miura, Takashi; Kumobayashi, Hidenori Advanced Synthesis and Catalysis, 2001 , vol. 343, # 3 p. 264 - 267]

Catalytic, enantioselective aldol additions with methyl and ethyl acetate O-silyl enolates: a chiral tridentate chelate as a ligand for titanium (IV)

[Journal of the American Chemical Society, , vol. 116, # 19 p. 8837 - 8838]

Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes

[Journal of the American Chemical Society, , vol. 127, # 11 p. 3774 - 3789]

Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides: Diastereoselective and Enantioselective Substitutions

[Journal of Organic Chemistry, , vol. 61, # 14 p. 4542 - 4554]

Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides: Diastereoselective and Enantioselective Substitutions

[Journal of Organic Chemistry, , vol. 61, # 14 p. 4542 - 4554]

More Articles...