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Synthesis of Isopropenylcyclopropanes − Revision of the Relative Configuration of Cyclopropyl Ketones Obtained by 1,3‐Elimination of γ‐Epoxy Ketones
Author(s) -
Cossy Janine,
Blanchard Nicolas,
Meyer Christophe
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200101)2001:2<339::aid-ejoc339>3.0.co;2-j
Subject(s) - cyclopropanation , chemistry , stereoselectivity , bicyclic molecule , intramolecular force , reactivity (psychology) , hydroxymethyl , allylic rearrangement , ketone , stereochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Efficient stereoselective routes towards isopropenylcyclopropanes have been devised. Secondary cis ‐isopropenylcyclopropylcarbinols have been obtained either by regio‐ and stereoselective hydroxy‐directed cyclopropanation of the corresponding dienols or from bicyclic cyclopropyl lactones derived from intramolecular cyclopropanation of allylic diazoacetates. Contrary to previous reports, base‐induced 1,3‐elimination of γ‐epoxy ketones has been shown to afford trans ‐2‐(hydroxymethyl)cyclopropyl ketones, and the reactivity of these compounds has been reinvestigated.