MilliporeSigma
  • Home
  • Search Results
  • Construction of spiro-fused 2-oxindole/α-methylene- γ-butyrolactone systems with extremely high enantioselectivity via indium-catalyzed amide allylation of N-methyl isatin.

Construction of spiro-fused 2-oxindole/α-methylene- γ-butyrolactone systems with extremely high enantioselectivity via indium-catalyzed amide allylation of N-methyl isatin.

Organic letters (2013-11-15)
Yusuke Murata, Masaki Takahashi, Fumitoshi Yagishita, Masami Sakamoto, Tetsuya Sengoku, Hidemi Yoda
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Indium, wire, diam. 2.0 mm, 99.995% trace metals basis
Sigma-Aldrich
Indium, foil, thickness 1.0 mm, 99.999% trace metals basis
Sigma-Aldrich
2-Oxindole, 97%
Sigma-Aldrich
Indium, foil, thickness 0.1 mm, ≥99.995% trace metals basis
Sigma-Aldrich
Indium, foil, thickness 0.5 mm, 99.99% trace metals basis
Sigma-Aldrich
Indium, wire, diam. 1.0 mm, 99.995% trace metals basis
Sigma-Aldrich
Indium, foil, thickness 0.25 mm, 99.995% trace metals basis
Sigma-Aldrich
γ-Butyrolactone, ReagentPlus®, ≥99%
Sigma-Aldrich
Indium, beads, diam. 2-5 mm, 99.999% trace metals basis
Sigma-Aldrich
Indium, beads, diam. 2-5 mm, ≥99.9% trace metals basis
Sigma-Aldrich
Indium, wire, diam. 0.5 mm, 99.995% trace metals basis
Sigma-Aldrich
Indium, pieces, 99.99% trace metals basis
Sigma-Aldrich
Indium, rod, diam. 6 mm, ≥99.999% trace metals basis
Sigma-Aldrich
Indium, wire, diam. 1.0 mm, 99.99% trace metals basis
Sigma-Aldrich
Indium, foil, thickness 0.5 mm, 99.999% trace metals basis
Sigma-Aldrich
Indium, powder, 99.99% trace metals basis
Sigma-Aldrich
Indium, wire, diam. 0.25 mm, 99.999% trace metals basis
Sigma-Aldrich
Indium, foil, thickness 0.25 mm, 99.99% trace metals basis
Sigma-Aldrich
4-Hydroxybutanoic acid lactone, ≥98%, FCC, FG
Sigma-Aldrich
Indium, powder, −60 mesh, 99.999% trace metals basis
Sigma-Aldrich
Indium, wire, diam. 1.5 mm, 99.99% trace metals basis
Sigma-Aldrich
Indium, bars, 99.95%
Sigma-Aldrich
Indium, powder, −100 mesh, 99.99% trace metals basis
Sigma-Aldrich
Indium, foil, thickness 0.127 mm, 99.99% trace metals basis
Sigma-Aldrich
α-Methylene-γ-butyrolactone, 97%
Sigma-Aldrich
Isatin, 97%