Key result
Uncatalyzed Staudinger reaction successfully synthesizes C3-position adamantyl-substituted β-lactams yielding predominantly trans-products.
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No immediate clinical implications; leaves open further evaluation of adamantyl β-lactams for therapeutic use.
A series of C3-position adamantyl-substituted β-lactams were synthesized via uncatalyzed Staudinger reaction between adamantylketene generated by thermal Wolff rearrangement of the corresponding diazo ketone and various imines. The stereochemical outcome of the reaction was mainly the formation of trans-products, a result attributed to a two-step mechanism leading to the most stable products.
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Liu et al. (2013) studied this question. An uncatalyzed Staudinger reaction between adamantylketene and various imines successfully synthesized C3-position adamantyl-substituted β-lactams, yielding predominantly trans-products.
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