Synthesis and reaction of 1-azabicyclo[3.1.0]hexane.
The effective formation of 1-azabicyclo[3.1.0]hexane (5) by treatment of 2-(bromomethyl)pyrrolidine hydrobromide (4) with n-BuLi was established, with the reaction occurring by a rational reaction pathway via the open chain transition state 8 based on intermolecular Br...Li(+) coordination (SN2 process). The reaction of 5 with electrophiles 13a-n gave the corresponding pyrrolidines 14a-n and piperidine 6, 15a-g, i-n. The selectivity of the products in this reaction appeared to be controlled by equilibrium.
Hayashi
Kazuhiko
K
College of Pharmacy, Kinjo Gakuin University, Nagoya 463-8521, Japan. hayashi@kinjo-u.ac.jp
Kujime
Eiko
E
Katayama
Hajime
H
Sano
Shigeki
S
Shiro
Motoo
M
Nagao
Yoshimitsu
Y
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006586:Hexanes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry
C545779:1-azabicyclo(3.1.0)hexane; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006586:Hexanes; D009942:Organometallic Compounds; D011759:Pyrrolidines; C434823:n-butyllithium