- Chiral linker. Part 4: Diastereoselective addition of RZnX to α-keto esters using m-hydrobenzoin derived chiral auxiliaries in solution and on solid support and their application in the stereoselective synthesis of frontalin
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Two recently reported, m-hydrobenzoin derived open chain chiral auxiliaries, which were developed for application in either solution or immobilized on a solid support, were tested in the diastereoselective addition of RZnX to their corresponding phenylglyoxylates and pyruvates, respectively, resulting in diastereoisomeric excesses of up to >98% de. The optimized procedure was applied in the stereoselective synthesis of frontalin, the aggregation pheromone of pine bark beetles of the Dendroctonus family, by the use of both the solution phase and the polymer supported chiral auxiliary.
- Schuster, Christian,Knollmueller, Max,Gaertner, Peter
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p. 2430 - 2441
(2007/10/03)
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- Synthesis of novel chiral hydrobenzoin mono-tert-butyl ethers derived from m-hydrobenzoin and their application as chiral auxiliaries in the diastereoselective reduction of α-keto esters
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Three m-hydrobenzoin derived chiral hydrobenzoin mono-tert-butyl ethers were synthesized by a new reaction pathway and tested as chiral auxiliaries in the L-selectride mediated stereoselective reduction of their corresponding phenyl glyoxylates. As a result, improved stereoselectivities of up to a ratio of 92:8 compared to 84:16 with the initially examined analogous benzyl ether were achieved.
- Schuster, Christian,Broeker, Joachim,Knollmueller, Max,Gaertner, Peter
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p. 2631 - 2647
(2007/10/03)
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