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

Unprecedented nucleophilic substitution reactions of 2,3-epoxy-1-alkanols with alkyl- and alkynylaluminum ate complexes have been studied and demonstrated to occur at the C2 position with extremely high stereoselectivity, i.e., with exactly reversed regioselectivity to that obtained in the substitut...

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Published inOrganic letters Vol. 3; no. 11; pp. 1765 - 1767
Main Authors Sasaki, Minoru, Tanino, Keiji, Miyashita, Masaaki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.05.2001
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC EPOXIDATION
EPOXIDES
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Summary:Unprecedented nucleophilic substitution reactions of 2,3-epoxy-1-alkanols with alkyl- and alkynylaluminum ate complexes have been studied and demonstrated to occur at the C2 position with extremely high stereoselectivity, i.e., with exactly reversed regioselectivity to that obtained in the substitution reactions by normal organoaluminum reagents, resulting in the formation of the C2-alkyl and C2-alkynyl substitution products in excellent yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol010062+