SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 19, 2008, Pages 2997-3000

Organocatalytic asymmetric 1,3-dipolar cycloaddition of nitrones to nitroolefins

(4) Du, Wei a Liu, Yan Kai a Yue, Lei a Chen, Ying Chun a

a SICHUAN UNIVERSITY (China)

Author keywords

Dipolar cycloaddition; Nitrones; Nitroolefins; Orgaoncatalysis; Thiourea

Indexed keywords

ALKENE DERIVATIVE; NITRO DERIVATIVE; NITRONE DERIVATIVE; THIOUREA;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYCLOADDITION; DIASTEREOISOMER; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 57649134975 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1087300 Document Type: Article

Times cited : (25)

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- General Procedure for the Asymmetric 1,3-Dipolar Cycloaddition Reaction Catalyst 1j (6.6 mg, 0.01 mmol, 10 mol, nitrone 2a (20.0 mg, 0.1 mmol) and 4 Å MS (50 mg) were stirred in redistilled MTBE (0.4 mL) at 0°C. Then nitroolefin 3a (14.0 mg, 0.12 mmol) in MTBE (0.1 mL) was added. After 6 d, product 4a was isolated by FC on SiO 2 eluted with EtOAc-PE as an oil; 24.5 mg, 79% yield; R f, 0.5 (PE-EtOAc, 15:1, α]D20 -101.3 (c 1.00 in CH2Cl2, 82% ee, determined by HPLC analysis [Daicel chiralcel OD, n-hexane-i-PrOH (95:5, 1.0 mL/min, 1, 254 nm, tR(major, 7.70 min, tR(minor, 11.16 min, 1H NMR (400 MHz, CDCl3, δ, 7.44-7.41 (m, 2 H, 7.35-7.33 (m, 3 H, 7.21-7.17 (m, 2 H, 7.04-6.98 (m, 3 H, 5.29 (dd, J, 9.2, 7.2 Hz, 1 H, 4.80 (t, J, 7.2 Hz, 1 H, 4.74 d
- 3 + Na: 335.1372; found: 335.1320.

69
- 57649137652
- General Procedure for the Synthesis of 2,3-Diamino-propanol 5 Compound 4a (31 mg, 0.1 mmol, 99% ee) and NiCl2·6H 2O (100 mg, 0.4 mmol) were stirred in MeOH (1 mL) and THF (0.5 mL) at r.t. for 10 min. Then NaBH4 (33 mg, 0.9 mmol) was added in portions at 0°C. After stirring for 5 min, EtOAc (5 mL) and H2O (5 mL) were added. After filtration, the filtrate was extracted with EtOAc (2 x 10 mL, The combined organic layers were dried over Na2SO4 and concentrated. The residue and (Boc)2O (26 mg, 0.12 mmol) were dissolved in CH2Cl2 and stirred for 2 h. The solvent was then removed in vacuo, and the residue was purified by flash chromatography on SiO2 (EtOAc-PE) to give N-Boc- diaminopropanol 5 as an oil; 35 mg, 91% yield for two steps; Rf= 0.4 (PE-EtOAc, 5:1, α]D20 +18.6 c 0.70 in CH2
- 3 + H: 385.2491; found: 385.2453.

70
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- These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via
- CCDC-700901 (6) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
- CCDC-700901 (6) contains the supplementary crystallographic data for this paper

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