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Synlett

Volumn , Issue 6, 2008, Pages 857-860

A novel chiral H′4-NOBIN schiff base for hetero-diels-alder reaction of danishefsky's diene with aldehydes

(5) Li, Xinsheng a Meng, Xiangyan a Su, Hong a Wu, Xiaohua a Xu, Dongcheng a

a ZHEJIANG NORMAL UNIVERSITY (China)

Author keywords

Asymmetric catalysis; Diels Alder reactions; Heterocycles; Schiff bases; Titanium

Indexed keywords

ALDEHYDE; ALKADIENE; DANISHEFSKY DIENE; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HETERO DIELS ALDER REACTION; HYDROGENATION; X RAY ANALYSIS;

EID: 42049091441 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1042913 Document Type: Article

Times cited : (7)

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32
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- Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 658558, R)-7, These data can be obtained free of charge via, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk
- Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 658558 [(R)-7]. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk.].

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36
- 42049121174
- General Procedure for Catalytic Enantioselctive Hetero-Diels-Alder Reaction A mixture of (S)-Schiff Base (19.7 mg, 0.05 mmol, Ti(Oi-Pr)4 in toluene (0.25 M, 0.1 mL, 0.025 mmol) and activated powdered 4 Å MS (40 mg) in toluene (1 mL) was stirred for 2 h at 50°C. The red solution was cooled to r.t. and naproxen (5.8 mg, 0.025 mmol, aldehyde (0.25 mmol, and Danishefsky's diene (60 μL, 0.3 mmol) were added sequentially. The mixture was stirred for 12 h at r.t. before quenched with TFA (0.2 mL, After stirring for additional 30 min, the mixture was neutralized with sat. NaHCO3 (3 mL, After filtration through a plug of Celite, the organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 5 mL, The combined organic layers were dried over anhyd Na 2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc-hexane, 1:4) to give the products for 1H NMR a
- 1H NMR and HPLC analysis.

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