Stereoselective synthesis of spirooxindoles by palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins.
A new synthetic method of spirooxindole derivatives has been developed by way of a palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins. By employing a newly prepared phosphoramidite ligand, the reaction proceeds smoothly with excellent diastereoselectivity. Preliminary results of its application to asymmetric catalysis using a chiral phosphoramidite ligand are also described.
Shintani
Ryo
R
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. shintani@kuchem.kyoto-u.ac.jp
Hayashi
Shin-ya
SY
Murakami
Masataka
M
Takeda
Momotaro
M
Hayashi
Tamio
T
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007211:Indoles; D011753:Pyrones; D013141:Spiro Compounds; C052207:delta-valerolactone; D010165:Palladium; D007510:Isatin