Construction of Spiro-Fused 2-Oxindole/α-Methylene- γ-Butyrolactone Systems with Extremely High Enantioselectivity via Indium-Catalyzed Amide Allylation of N-Methyl Isatin
作者： Yusuke Murata , Masaki Takahashi , Fumitoshi Yagishita , Masami Sakamoto , Tetsuya Sengoku
DOI: 10.1021/OL403014U
关键词: Enantiopure drug 、 α methylene γ butyrolactone 、 Catalysis 、 2-oxindole 、 Isatin 、 Medicinal chemistry 、 Amide 、 Stereochemistry 、 Enantioselective synthesis 、 Chemistry 、 Indium
摘要: 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 use indium-catalyzed asymmetric amide allylation N-methyl isatin with functionalized allylstannanes, which can lead to antineoplastic spirocyclic lactones almost enantiopure forms.
acs.org
sci-hub.se 参考文章(21)
Ponnusamy Shanmugam, Vadivel Vaithiyanathan, Stereoselective synthesis of 3-spiro-α-methylene-γ-butyrolactone oxindoles from Morita–Baylis–Hillman adducts of isatin Tetrahedron. ,vol. 64, pp. 3322- 3330 ,(2008) , 10.1016/J.TET.2008.02.002
Christiane Marti, Erick M. Carreira, Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids European Journal of Organic Chemistry. ,vol. 2003, pp. 2209- 2219 ,(2003) , 10.1002/EJOC.200300050
Kazuhiko Tanaka, Hidemi Yoda, Yutaka Isobe, Aritsune Kaji, Asymmetric synthesis of γ-alkayl-α-methylene-γ-butyrolactones via 1,6-remote induction using 2-[(tributylstannyl) methyl]propenamides Tetrahedron Letters. ,vol. 26, pp. 1337- 1340 ,(1985) , 10.1016/S0040-4039(00)94887-1
Ned D. Heindel, John A. Minatelli, Synthesis and antibacterial and anticancer evaluations of α ‐ methylene ‐γ ‐ butyrolactones Journal of Pharmaceutical Sciences. ,vol. 70, pp. 84- 86 ,(1981) , 10.1002/JPS.2600700117
Elisa G. Gutierrez, Casey J. Wong, Aziza H. Sahin, Annaliese K. Franz, Enantioselective and regioselective indium(III)-catalyzed addition of pyrroles to isatins. Organic Letters. ,vol. 13, pp. 5754- 5757 ,(2011) , 10.1021/OL202329S
Yoshinori. Yamamoto, Naoki. Asao, SELECTIVE REACTIONS USING ALLYLIC METALS Chemical Reviews. ,vol. 93, pp. 2207- 2293 ,(1993) , 10.1021/CR00022A010
Anke Bachelier, Ralf Mayer, Christian D. Klein, Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA. Bioorganic & Medicinal Chemistry Letters. ,vol. 16, pp. 5605- 5609 ,(2006) , 10.1016/J.BMCL.2006.08.021
Kazuhiko Tanaka, Hidemi Yoda, Yutaka Isobe, Aritsune Kaji, Asymmetric synthesis of α-methylene-γ-butyrolactones using chiral N-monosubstituted 2-[(tributylstannyl)methyl]propenamides Journal of Organic Chemistry. ,vol. 51, pp. 1856- 1866 ,(1986) , 10.1021/JO00360A038
Hisao. Nishiyama, Hisao. Sakaguchi, Takashi. Nakamura, Mihoko. Horihata, Manabu. Kondo, Kenji. Itoh, Chiral and C2-symmetrical bis(oxazolinylpyridine)rhodium(III) complexes: effective catalysts for asymmetric hydrosilylation of ketones Organometallics. ,vol. 8, pp. 846- 848 ,(1989) , 10.1021/OM00105A047
Qi-Lin Wang, Lin Peng, Fei-Ying Wang, Ming-Liang Zhang, Li-Na Jia, Fang Tian, Xiao-Ying Xu, Li-Xin Wang, An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles. Chemical Communications. ,vol. 49, pp. 9422- 9424 ,(2013) , 10.1039/C3CC45139A