Atroposelective attack of nucleophiles on 2-formyl-1-naphthamides and their derivatives: Chelation and non-chelation control

Jonathan Clayden*, Catherine McCarthy, Neil Westlund, Christopher S. Frampton

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

41 Citations (Scopus)

Abstract

Organometallic nucleophiles attack 2-formyl-l-naphthamides to give secondary alcohols with widely varying atroposelectivity. By careful choice of reagent, selectivities of up to >99:1 in favour of either the anti or the syn atropisomer can be obtained. Ethers and amines may be synthesised atroposelectively from acetals or imines. The sense of the selectivity is determined by the reactive conformation of the Ar-CHO bond, itself dependent on the coordinating and chelating ability of the nucleophile's counterion. The roles of conformation, Lewis acids, and chelation/non-chelation control in relation to stereoselectivity are discussed.

Original languageEnglish
Pages (from-to)1363-1378
Number of pages16
JournalPerkin 1
Issue number9
DOIs
Publication statusPublished - 18 Apr 2000

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