Abstract
The stereochemistry of the Peterson olefination reaction between PhHSiMe3 and PhCHO has been studied under a wide variety of conditions with excellent reproducibility and extremely high yields. The effects of counterion, solvent, added salts, variation of the carbanion-forming base, and temperature have been investigated. The product stereochemistry is remarkably insensitive to the reaction conditions. The results lead to a new method of analysis of steric approach control based on the angle of approach as defined by Dunitz and Baldwin. The method involves analysis of ‘primary’ and ‘secondary’ transition-state interactions. This analysis should be generally applicable to carbanion additions in which chelation is insignificant.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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