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Journal Article

Cram Selectivity in the Reaction of 2-Phenylpropanal with Alkyllithium Reagents: Myth and Reality

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Reetz,  Manfred T.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Stanchev,  Stephan
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Haning,  Helmut
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Reetz, M. T., Stanchev, S., & Haning, H. (1992). Cram Selectivity in the Reaction of 2-Phenylpropanal with Alkyllithium Reagents: Myth and Reality. Tetrahedron, 48(33), 6813-6820. doi:10.1016/S0040-4020(01)89872-0.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0023-CA54-3
Abstract
The reaction of racemic 2-phenylpropanal with methyl- and n-butyllithium was studied in detail. Factors such as temperature, solvent, rate of addition, presence of salts, scale-up and source of reagents were carefully examined. Cram-selectivities of 90 –94% were routinely reached under standard conditions (THF, −78°C), which is significantly higher than previously reported for these classical reactions