SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 10, 2007, Pages 1605-1609

Organocatalytic enantioselective synthesis of secondary α-hydroxycarboxylates

(2) Dodda, Rajasekhar a Zhao, Cong Gui a

a UNIVERSITY OF TEXAS AT SAN ANTONIO (United States)

Author keywords

hydroxycarboxylate; Aldol reaction; Enantioselectivity; Ethyl glyoxylate; Ketones; Organocatalysis

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; DIPEPTIDE; ETHYLGLYOXYLATE; GLYOXYLIC ACID DERIVATIVE; KETONE DERIVATIVE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; ORGANIC CHEMISTRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 34347371630 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-982552 Document Type: Article

Times cited : (28)

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- General Experimental Procedure To a stirred solution of ethyl glyoxylate (51.0 mg, 0.5 mmol) and the ketone (0.25 mL) in CHCl3 (0.25 mL) was added catalyst 5 (13.6 mg, 0.05 mmol) at -10°C. The reaction mixture was stirred at this temperature for 24-72 h. The solvent was then evaporated under vacuum and the residue was purified by flash chromatography (EtOAc-hexane, 1:2) over silica gel to furnish the desired secondary -hydroxycarboxylate as a pure compound. 1H NMR and 13C NMR data of new compounds are collected below. Compound 5: 1H NMR (500 MHz, CDCl3, 0.83 (t, J, 7.5 Hz, 6 H, 1.90-1.92 (m, 1 H, 1.99 (s, 3 H, 2.06-2.11 (m, 2 H, 2.96 (d, J, 3.0 Hz, 2 H, 3.79 (t, J, 8.0 Hz, 1 H, 4.12 (q, J, 4.5 Hz, 1 H, 5.08 (d, J, 2.5 Hz, 1 H, 8.10 (d, J, 9.5 Hz, 1 H, CONH) ppm. 13C NMR 125 MHz, CDCl3, 18.3, 19.8, 21.7, 31.1, 37.6, 53.0, 57
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