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Volumn 5, Issue 2, 2008, Pages 79-81

A new, readily available double-component system for asymmetric Henry reaction

Author keywords

nitroalcohol; Asymmetric synthesis; C C bond formation; Chiral amino alcohol; Double component catalytic system; Henry reaction

Indexed keywords

EID: 46049083774 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017808783743876 Document Type: Article

Times cited : (6)

References (19)

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- Representative procedure: Compound 3 (0.14g, 0.3 mmol) was allowed to mix with Cu(OAc)2-H2O (0.06 g, 0.3 mmol) in THF (2 mL) at room temperature and stirred for 1h, and then benzaldehyde (0.31 mL, 3 mmol) and nitromethane (1.62 mL, 30 mmol) were sequentially added. The mixture was heated to 45 °C and stirred for 72 h, cooled to room temperature, and 0. 1 M HCI was added. The organic phase was separated, and the water phase was extracted with EtOAc (45 mL, The combined organic phases were washed with saturated NaCl, dried over anhydrous Na2SO4 and concentrated, and the residue was purified by column chromatography to give 1-phenyl-2-nitro-ethanol(Yield 0.12 g, 24, α]D2D=+24.6 (c 0.20, CH2l2, 1H NMR (CDCl3, 300 MHz) δ (ppm, 7.39 (m, 5H, 5.47-5.42 (m, 1H, 4.64-4.47 (m, 2H, 2.90 (d, J= 3.9 Hz, 1H, IR (KBr, cm-1):3629, 3421, 3065, 3033, 2918, 1670, 1
- r 13.4 min; 53% ee.

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19
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- A possible mechanism for the reaction
- A possible mechanism for the reaction:

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