Tetrahedron Letters p. 1819 - 1822 (1999)
Update date:2022-08-03
Topics:
Coldham, Iain
Fernandez, Joan-Carles
Snowden, David J.
Cyclizations of α-amino-organolithiums, derived by tin-lithium exchange, which proceed via a stereoselective two-electron process and totally regiospecific 5-exo-trig ring closure, have been extended to the preparation of the 7-azabicyclo[2.2.1]heptane ring system. Cyclization occurs from either the cis or the trans isomer of 5-allyl-2-tri-n-butylstannyl-N- benzylpyrrolidine to give only the exo product as a single diastereomer in isolated yields up to 83%.
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