John N. Bonfiglio

Hydroboration-carbonylation of bisolefinic amines: a facile synthesis of δ-coniceine

Abstract Treatment of N-allyl-N-3-butenyl-N-Cbz-amIne ( 1 ) with thexyl borane followed by cyanidation affords an azacyclononanone 2 in 35% yield which can be transformed into δ-coniceine ( 3 ) by catalytic reduction.

A Facile One-Pot Synthesis of 1-Thiacycloöctan-5-one 1-Oxide

Abstract The preparation of medium-sized heterocyclic rings by closure reactions of acyclic species has been limited to the Dieckman reaction,1 the acyloin reaction,2 lactone formation,3 and recently a three carbon ylide based ring expansion.4 We have been investigating the hydroboration-carbonylation of α,ω-bis-olefinic hetero-atom containing dienes and wish to report a facile one-pot synthesis of 1-thiacyclooctan-5-one 1-oxide (2) from allyl sulfide (1) using chloroborane-methyl sulfide.