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Organocatalytic Addition on 1,2‐Bis(sulfone)vinylenes Leading to an Unprecedented Rearrangement
Author(s) -
Quintard Adrien,
Alexakis Alexandre
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901535
Subject(s) - sulfone , chemistry , pyrrolidine , adduct , organocatalysis , rearrangement reaction , alkylation , organic chemistry , catalysis , enantioselective synthesis
An unprecedented rearrangement of 1,2‐bis(sulfone)vinylenes used in aminocatalysis led to the formation of highly useful gem ‐disulfones (see scheme). By using aminal–pyrrolidine organocatalysts, the 1,2‐sulfone shift was generalised, leading to highly versatile adducts using both ketones and aldehydes. It represents a valuable alternative for the α‐alkylation of carbonyl compounds.