Ontology highlight
ABSTRACT:
SUBMITTER: Lu P
PROVIDER: S-EPMC4480775 | biostudies-literature | 2015 Jun
REPOSITORIES: biostudies-literature
Tetrahedron letters 20150601 23
A rare 5-exo-dig S<sub>N</sub>i' cyclization with magnesiated and lithiated nitriles affords a <i>cis-</i>fused hydrindane bearing an exocyclic allene. The cyclization of the dilithiated nitrile pits a stereoelectronic preference for a <i>trans-</i>hydrindane against a cyclization through a less strained transition structure to the corresponding <i>cis</i>-hydrindane. Computational modeling suggests that the dilithiated nitrile cyclizes to a <i>cis-</i>hydrindane because the preferred transition ...[more]