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The Epoxy‐Ramberg–Bäcklund Reaction (ERBR): A Sulfone‐Based Method for the Synthesis of Allylic Alcohols
Author(s) -
Evans Paul,
Johnson Paul,
Taylor Richard J. K.
Publication year - 2006
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/ejoc.200500956
Subject(s) - allylic rearrangement , chemistry , epoxy , sulfone , organic chemistry , scope (computer science) , catalysis , computer science , programming language
The epoxy‐Ramberg–Bäcklund reaction (ERBR) is outlined, in which α,β‐epoxy sulfones are converted into a range of mono‐, di‐ and tri‐substituted allylic alcohols, on treatment with base. Modification of this method enabled the preparation of enantio‐enriched allylic alcohols following the diastereoselective epoxidation of enantio‐enriched vinyl sulfones that were accessed efficiently from the chiral pool. The scope, optimisation and limitations of the ERBR as a method for the preparation of allylic alcohols are discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)