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Liebigs Annalen der Chemie

Stereoselective synthesis of alcohols, XL. Stereoselective cyclization of 7??oxo??2??heptenylboronates

RW Hoffmann, G Niel

文献索引:Hoffmann, Reinhard W.; Niel, Gilles Liebigs Annalen der Chemie, 1991 , # 11 p. 1195 - 1201

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被引用次数: 11

摘要

Abstract Intramolecular allylboration reaction of 7-oxo-2-heptenyl boronates leads to 2- vinylcyclopentanols. The cyclization proceeds in a stereospecific manner, such that the (E)- allylboronate 8 is converted into trans-2-vinylcyclopentanol (2) and the (Z)-allylboronate 10 into cis-2-vinylcyclopentanol (3). Asymmetric induction originating from stereogenic centers placed between the boronate and the aldehyde function has been found to be low.