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Selected Transformations of 6‐Cyclopropylidene‐5‐oxaspiro[2.3]hexan‐4‐one, a Highly Strained Tricyclic β‐Lactone
Author(s) -
Wulferding Andreas,
Jankowski JöRg H.,
Hoffmann H. Martin R.
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270716
Subject(s) - chemistry , lactone , steric effects , tricyclic , phenols , stereochemistry , organic chemistry
The title lactone 2 acylates a variety of amines including phenylalanine, sterically hindered alcohols, and phenols. With activated non‐enolizable carbonyl compounds, bis‐spiro 6‐membered β‐keto lactones are formed. Oxidative rearrangement of 2 affords bis‐spiro lactones 12 and 13 .