Title:
OPTICALLY ACTIVE ALCOHOL AND CARBOXYLIC ACID ESTER THEREOF
Document Type and Number:
Japanese Patent JP3770678
Kind Code:
B2
Abstract:
PROBLEM TO BE SOLVED: To obtain the subject new compound having an α-H and useful for the synthesis of an optically active anti-aldol by enolizing in the presence of boron triflate and an amine, and then reacting with an aldehyde.
SOLUTION: This optically active alcohol is a new compound expressed by formula I (R1 to R6 are each H, an alkyl, etc.), e.g. 2-(N-methylenesulfonyl) amino-1-phenyl-1-propanol. The method for producing the compound of formula I is constituted by e.g. using norephedrine as a raw material, performing an N-sulfonylation reaction of the raw material by mesitylene sulfonylchloride and (C2H5)3N in CH2Cl2 to form a compound of formula II, then performing an N-benzylation reaction of the above compound with benzyl bromide and K2CO3 in CH3CN to form an optically active alcohol of formula III, and esterifying the alcohol with propionyl chloride and pyridine in CH2Cl2 to form a carboxylic acid ester expressed by formula IV.
Inventors:
Atsuko Abiko
Liu Jifeng
Liu Jifeng
Application Number:
JP35242396A
Publication Date:
April 26, 2006
Filing Date:
December 13, 1996
Export Citation:
Assignee:
Kao Corporation
International Classes:
C07B53/00; C07C215/00; C07C31/135; C07C31/20; C07C33/14; C07C219/00; C07C311/16; (IPC1-7): C07C215/00; C07C31/135; C07C31/20; C07C33/14; C07C219/00; C07C311/16; //C07B53/00; C07M7:00
Other References:
Concerning the Boron-Mediated Aldol Reaction of Carboxylic Esters,J. Org. Chem.,1996年 5月10日,1996,Vol.61 No.8,p2590-2591
Stereoselective Aldol Rections. Reaction of Chiral Ester Titanium Enolate with Aldehydes,Tetrahedron Letters,1992年,Vol.33,No.4,p457-460
Synthesis of Enantiomerically Pure Anti-Aldols,J.Am.Chem.Soc.,1996年 4月 3日,Vol118,No.10,p2527-2528
Stereoselective Aldol Rections. Reaction of Chiral Ester Titanium Enolate with Aldehydes,Tetrahedron Letters,1992年,Vol.33,No.4,p457-460
Synthesis of Enantiomerically Pure Anti-Aldols,J.Am.Chem.Soc.,1996年 4月 3日,Vol118,No.10,p2527-2528
Attorney, Agent or Firm:
Takehiko Yoshimura
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