Regioselective Alkyl and Alkynyl Substitution Reactions of Epoxy Alcohols by the Use of Organoaluminum Ate Complexes: Regiochemical Reversal of Nucleophilic Substitution Reactions

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1765-1767

  Sasaki, Minoru ^a   Tanino, Keiji ^a   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

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EID: 0012555742     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010062+     Document Type: Article

References (27)

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20. Treatment of the crude products with sodium periodate followed by column chromatography afforded the 1,3-diols in pure form. The stereo-chemistry of the products was confirmed by comparison with authentic samples which were prepared by the reaction of organocopper reagents.
21. 3b
22. This result was also found to be far better than that obtained in the reactions with dimethylcupurate (selectivity of C2/C3 = 70-82:18-30).
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