Abstract
The desymmetrization of symmetric compounds is a useful approach to obtain chiral building blocks. Readily available precursors with a prochiral unit could be converted into complex molecules with multiple stereogenic centers in a single step. In this review, recent advances in the desymmetrization of symmetric dienes in the diastereotopic group differentiating reaction and its synthetic application are presented.
Highlights
The desymmetrization of meso compounds has become one of the most powerful strategies in organic synthesis [1]
A broad range of reactions have been developed for the desymmetrization of cyclohexadienes, and synthetic applications to natural product synthesis have been reported
We have developed an asymmetric synthesis of the chiral 1,4- and 1,5-diols by the diastereoselective intramolecular haloetherification reaction of the ene acetals 58, prepared from the C2-symmetric diols and ene aldehydes, involving the remote asymmetric induction [36,37]
Summary
The desymmetrization of meso compounds has become one of the most powerful strategies in organic synthesis [1] It allows the formation of multiple chiral centers in a single step and offers an entry to a wide range of stereochemically complex molecules including natural products. Substituted 1,4-cyclohexadienes have a great potential for the desymmetrization reactions [3,4] These compounds are prepared by the Birch reduction/alkylation sequence of aromatic. A broad range of reactions have been developed for the desymmetrization of cyclohexadienes, and synthetic applications to natural product synthesis have been reported. We will highlight the recent reports for the desymmetrization of dienes by diastereotopic group differentiating reactions in a stereoselective manner and its applications (Figure 1).
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