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Letters in Organic Chemistry

Volumn 6, Issue 4, 2009, Pages 329-331

Salan-vanadium catalyzed enantioselective desymmetrization of meso-epoxides with aromatic thiols

(5) Sun, Jiangtao a Gu, Weijin b Huang, Yijun a Pan, Xu a Zhu, Chengjian a,c

a NANJING UNIVERSITY (China)

b NANJING NORMAL UNIVERSITY (China)

c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

Asymmetric catalysis; Enantioselectivity; Epoxides; Ring opening; Thiols; Vanadium

Indexed keywords

EID: 69549113079 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017809788489990 Document Type: Article

Times cited : (1)

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- 2. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography to furnish the corresponding hydroxyl sulfides. The enantiomeric purity was determined by HPLC analysis using a Daicel Chiracel OD-H column or OB-H column
- 2. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography to furnish the corresponding hydroxyl sulfides. The enantiomeric purity was determined by HPLC analysis using a Daicel Chiracel OD-H column or OB-H column

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- Ligand 3b was synthesized according to the following procedure: Under an argon atmosphere, 1.5 mL anhydrous DMF was added dropwise into a mixture of NaH (1.5 g, 25 mmol) and 15 mL anhydrous THF in a Schlenk tube. Then the mixture was stirred for 10 min and 2a (1.62 g, 5 mmol) was added. After stirred for another 30 min, bromobenzyl (1.3 mL, 11 mmol) was added and the mixture was stirred for 8 h at 50 °C. Water (5 mL) was then added to quench the reaction and the aqueous layer was separated and extracted with ether (3 × 30 mL). The combined organic layer was dried over anhydrous sodium sulfate
- 3): δ 1.10-1.37 (m, 4H), 1.69- 1.82 (m, 2H), 2.07-2.10 (m, 1H), 2.23-2.29 (m, 1H), 2.60 (s, 2H), 3.41-3.46 (d, 1H), 3.55-3.59 (d, 1H), 3.75-3.82 (t, 3H), 3.98-4.02 (d, 1H), 4.96-5.11 (m, 4H), 6.91-6.93 (m, 4H), 7.21-7.27 (m, 3H), 7.29-7.34 (m, 3H), 7.40-7.47 (m, 10H). MS (EI): 505(M-1, 16), 399(26), 94(5), 213(3), 197(17), 107(4), 106(2), 91(100), 65(2).

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