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Volumn , Issue 20, 2009, Pages 3279-3282

A chiral bifunctional sulfonamide as an organocatalyst: Alcoholysis of σ-symmetric cyclic dicarboxylic anhydrides

Author keywords

Alcoholysis; Anhydrides; Asymmetric synthesis; Homogeneous catalysis; Sulfonamides

Indexed keywords

ACID ANHYDRIDE; BENZYL ALCOHOL; CHYMOTRYPSIN A; DICARBOXYLIC ANHYDRIDE; SERINE PROTEINASE; SULFONAMIDE; UNCLASSIFIED DRUG;

EID: 72249093169     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218374     Document Type: Article
Times cited : (24)

References (43)
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    • 72249089357 scopus 로고    scopus 로고
    • note
    • General Experimental Procedure for Chiral Sulfonamide 1 Catalyzed Alcoholysis of Cyclic Dicarboxylic Anhydrides To a solution of 3-phenylglutaric anhydride (2a, 190 mg, 1.0 mmol) and chiral sulfonamide 1 (25.8 mg, 0.05 mmol) in Et2O (10 mL) was added BnOH (125 mL, 1.2 mmol) at r.t. After stirring at r.t. for 20 h, the reaction mixture was treated with 10% HCl followed by extraction with CHCl3. The extract was dried over anhyd MgSO4, filtered, and concentrated in vacuo. To a solution of the residue in benzene MeOH (7:2, 9 mL) was added a solution of TMSCHN2 (2.0 M in Et2O, 1 mL, 2.0 mmol). After being stirred at r.t. for 15 min, the reaction mixture was evaporated in vacuo. The oily residue was purified by silica gel column chromatography [EtOAc n-hexane (1:4)] to afford methyl ester (S)-4a (286 mg, 92% yield, 87% ee) as a colorless oil. The ee (%) of (S)-4a was determined on a Chiralpak AD-H column [Daicel, eluent: n-hexane 2-PrOH (15:1), flow rate: 1 mL/min, detection: 254 nm]. The retention times were 12.5 min [minor isomer, (R)-4a] and 13.8 min [major isomer, (S)-4a], respectively. The absolute configuration of (S)-4a was explicitly determined by its chemical conversion to thioester (S)-5 (Scheme 1).7 (Formula).
  • 41
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    • For details see Supporting Information.
    • For details see Supporting Information


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