Chemical Communications

Relaying stereochemistry through aromatic ureas: 1, 9 and 1, 15 remote stereocontrol

J Clayden, M Pickworth, LH Jones

Index: Clayden, Jonathan; Pickworth, Mark; Jones, Lyn H. Chemical Communications, 2009 , # 5 p. 547 - 549

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Citation Number: 9

Abstract

Encouraged by the apparent high level of conformational control in 7, we treated this aldehyde with a series of nucleophiles (Scheme 3), hoping to see correspondingly good levels of 1,9 remote stereoselectivity. The results are tabulated in Table 1, entries 1–12. In general, Grignard reagents gave moderate to good diastereoselectivity (entries 1, 5), which could be improved to some extent by reducing the temperature (entry 2) or by changing to a less coordinating solvent (entry ...