Synthesis of Furanes and 2,3-Dihydrofuranes
A R T I C L E S
emerged as a new and exciting field of research.12-14 These
useful and practical protocols enable efficient construction of
various important molecules of complex architecture under mild
reaction conditions and with a minimal number of manual
operations and purification procedures. Within this field it has
recently been demonstrated that R,ꢀ-unsaturated aldehydes can
participate in enantioselective organocatalytic one-pot cascade
reactions in a highly stereoselective fashion, providing valuable
chiral building blocks and offering access to various important
products.14,15a Given the importance of 2-hydroxyalkyl- and
2-aminoalkyl furanes and the lack of a general enantioselective
methodology for the preparation of electron-poor furane deriva-
Scheme 2. Classical Friedel-Crafts Approach for the Synthesis of
2-Hydroxyalkyl- and 2-Aminoalkyl Furanes
furanes rely mainly on the asymmetric Friedel-Crafts reaction
of substituted furane derivatives with aldehydes or imines
(Scheme 2).7 These powerful C-C bond-forming protocols have
been well studied over the years, becoming the method of choice
for the preparation of electron-rich 2-hydroxyalkyl- and 2-ami-
noalkyl furanes with high levels of stereoinduction. On the
contrary, methodologies for the stereoselective preparation of
nonracemic electron-poor furane and 2,3-dihydrofurane deriva-
tives are rare and in all cases based on the employment of
enantiomerically pure starting materials,6h,8,9 or a kinetic resolu-
tion of racemic starting materials.10,11 Moreover, most of these
methods give access to polyhydroxylated furanes, and no general
enantioselective approach leading to the formation of electron-
poor 2-hydroxyalkyl- and 2-aminoalkyl furanes exists in the
literature (Scheme 2). The preparation of electron-poor 2-ami-
noalkyl furanes appears especially challenging, since the only
methods for their synthesis disclosed in the literature require
the use of optically active furfuryl alcohols as the starting
materials.9 For these reasons the development of new and more
efficient synthetic strategies leading to the formation of these
important groups of compounds is of ongoing interest and seems
particularly valuable and challenging.
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