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Chiral oximes in asymmetric synthesis. Part 2.1 Addition of butyllithium to benzaldehyde O-(1-phenylalkyl)oximes

1997; Issue: 17 Linguagem: Inglês

10.1039/a700984d

2050-8255

P. T. Gallagher, James C. A. Hunt, Andrew P. Lightfoot, Christopher J. Moody,

Axial and Atropisomeric Chirality Synthesis

A series of benzaldoxime ethers PhCHNOCHRPh 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.