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Volumn , Issue 1, 2007, Pages 59-62

Aluminum iodide promoted highly Z-stereoselective synthesis of β-iodo Morita-Baylis-Hillman esters with ketones as aldol acceptors

(3) Lee, Sung Il a Hwang, Geum Sook b Ryu, Do Hyun a

a Sungkyunkwan University (South Korea)

b Korea Basic Science Institute (KBSI) (South Korea)

Author keywords

Aldol reactions; Aluminum iodide; Ketones; Morita Baylis Hillman adduct; Stereoselectivity

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALUMINUM ALLENOATE; ALUMINUM IODIDE; BETA IODO ALPHA(HYDROXYALKYL)ACRYLATE DERIVATIVE; ESTER DERIVATIVE; IODINE DERIVATIVE; KETONE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; BAYLIS HILLMAN REACTION; STEREOCHEMISTRY;

EID: 33846439385 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2006-958421 Document Type: Article

Times cited : (17)

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25
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- Experimental Procedure: CH2Cl2 (2.0 mL) was slowly added to an aluminum iodide (0.22 mmol) at -78 °C under N 2. Ethyl propiolate (0.24 mmol) and the ketone (0.20 mmol) were added sequentially. The reaction was monitored by TLC. After the reaction time indicated in Table 1, it was quenched with H2O (2.0 mL) and an aqueous layer was extracted with CH2Cl2. The combined organic phase was dried over Na2SO4 and the solvent was removed under vacuum. The crude product was purified by column chromatography (CH2Cl2-hexane 3:1) to provide a pure product, Z)-Ethyl 3-[4-(Trifluoromethyl)phenyl]-3-hydroxy-2-(iodomethylene)butanoate (Entry 13, IR: 3476, 2983, 1718, 1327, 1124, 845 cm-1. 1H NMR (500 MHz, CDCl3, δ, 7.60 (2 H, d, J, 8.0 Hz, 7.54 (2 H, d, J, 8.5 Hz, 7.24 (1 H, s, 4.17 (2 H, m, 4.08 1 H, brs, 1.70
- +], 331 (30), 216 (100), 108 (8).

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