Atroposelectivity in the reactions of laterally lithiated tertiary amides

DOI: 10.1016/S0040-4039(97)00401-2

Source and publish data:

Tetrahedron Letters p. 2561 - 2564 (1997)

Update date:2022-08-12

Topics:

Authors:

Clayden, Jonathan

Pink, Jennifer H.

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Article abstract of DOI:10.1016/S0040-4039(97)00401-2

Lateral lithiation - electrophilic quench of 2-substituted N,N-dialkyl-1-naphthamides proceeds with high levels of diastereoselectivity in favour of one atropisomer of the product. Similar atroposelectivity may be observed in the reactions of 2-substituted benzamides, provided the products are trapped at low temperature by a subsequent in situ ortholithiation - alkylation reaction.

Full text of DOI:10.1016/S0040-4039(97)00401-2

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Product name:Benzamide, 2-ethyl-N,N-bis(1-methylethyl)-

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