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20.5.1.7 Synthesis with Retention of the Functional Group

DOI: 10.1055/sos-SD-020-00774

Zhang, M.; Hanson, P. R.Science of Synthesis, (200720863.

General Introduction

This contribution covers material published since 1985 regarding the synthesis of alkyl alkanoates with retention of the functional group. Previously published information regarding this method group can be found in HoubenWeyl, Vol. 5/1, pp 702709. There are several functional group transformations that can be carried out in the presence of an ester group. This review will focus on several reactions, with the majority of examples falling into the CC bond-forming category, including the following: conjugate addition reactions and reductions (hydrogenations) of α,β-unsaturated esters, alkylations, metal-catalyzed cross couplings, cleavage reactions, oxidations, addition reactions of formates, ring opening of lactones, isomerizations, metathesis, transesterifications, and kinetic resolutions. As they fall outside the scope of this contribution and are covered in general terms in other volumes, cyclization reactions and epoxidations with ester functional groups are not included here.


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