Consecutive cyclization of allylaminoalkene by intramolecular aminolithiation-carbolithiation.
Consecutive cyclization of allylaminoalkenes by tandem aminolithiation-carbolithiation proceeded smoothly by using a lithium amide as a lithiating agent as well as protonating agent to give bicyclic amines, octahydroindolizine and hexahydro-1 H-pyrrolizine, in reasonably high yield and diastereoselectivity.
Tsuchida
Susumu
S
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Kaneshige
Atsunori
A
Ogata
Tokutaro
T
Baba
Hiromi
H
Yamamoto
Yasutomo
Y
Tomioka
Kiyoshi
K
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D000577:Amides; D000588:Amines; D054836:Indolizidines; D009942:Organometallic Compounds; D011758:Pyrroles; D008094:Lithium