Chiral oximes in asymmetric synthesis. Part 2.1 Addition of butyllithium to benzaldehyde O-(1-phenylalkyl)oximes
Abstract
A series of benzaldoxime ethers PhCH![[double bond, length as m-dash]](https://www.rsc.org/images/entities/char_e001.gif)
NOCHRPh 5 bearing a
chiral auxiliary on oxygen have been prepared to investigate the effect
of the auxiliary on the diastereoselectivity of the addition of
butyllithium to the oxime CN bond. By increasing the size of the
alkyl group R in the auxiliary, OCHRPh, an increase in de is observed,
with the best compromise between ready availability and high levels of
asymmetric induction in the product 6 being achieved with the oximes
derived from O-(1-phenylbutyl)hydroxylamine.
NOCHRPh 5 bearing a
chiral auxiliary on oxygen have been prepared to investigate the effect
of the auxiliary on the diastereoselectivity of the addition of
butyllithium to the oxime CN bond. By increasing the size of the
alkyl group R in the auxiliary, OCHRPh, an increase in de is observed,
with the best compromise between ready availability and high levels of
asymmetric induction in the product 6 being achieved with the oximes
derived from O-(1-phenylbutyl)hydroxylamine.
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