Bis(trimethylsilyl)methylamine (BSMA): tool or toy?

Bis(trimethylsilyl)methylamine, BSMA, an original primary amine, was proven to be the source of a large variety of N-bis(trimethylsilyl)methylamino derivatives that otherwise have to be prepared indirectly. Because of the bulkiness of the bissilylmethyl group, regio- and stereoselectivities resulted in appropriated examples. Apart from the potential biological properties associated with the Si-C-N framework, these derivatives were powerful synthetic intermediates. Special emphasis was given to the chemistry of corresponding imines. Cleavage of Si-C bonds or abstraction of the methine proton afforded alpha -nitrogen carbanions in very mild conditions. Application of these results to the beta -lactam chemistry allowed the introduction of new synthetic methodologies in this field. It results the (Me3Si)(2)CH- group could now be regarded as a Me3SiCH2- or a CH3- group or a proton equivalent.