Construction of spiro-fused 2-oxindole/α-methylene- γ-butyrolactone systems with extremely high enantioselectivity via indium-catalyzed amide allylation of N-methyl isatin.
A remarkably effective method allowing an extremely high enantioselective synthesis of the spiro-fused 2-oxindole/α-methylene-γ-butyrolactones is described. The key strategy lies in the use of indium-catalyzed asymmetric amide allylation of N-methyl isatin with functionalized allylstannanes, which can lead to the antineoplastic spirocyclic lactones in almost enantiopure forms.
Graduate School of Science and Technology, Shizuoka University , Department of Applied Chemistry, Graduate School of Engineering, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan, and Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University , 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
Yusuke
Y
Murata
Masaki
M
Takahashi
Fumitoshi
F
Yagishita
Masami
M
Sakamoto
Tetsuya
T
Sengoku
Hidemi
H
Yoda
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D007204:Indium / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D007211:Indoles; D009942:Organometallic Compounds; D000078183:Oxindoles; D013141:Spiro Compounds; D007204:Indium; C022960:2-oxindole; C014096:alpha-methylene gamma-butyrolactone; D007510:Isatin; D015107:4-Butyrolactone