Tandem Michael addition-ring transformation reactions of 3-hydroxyoxindoles/3-aminooxindoles with olefinic azlactones: direct access to structurally diverse spirocyclic oxindoles.
An efficient method for the direct construction of two classes of spirocyclic oxindoles by the reactions of 3-hydroxyoxindoles/3-aminooxindoles and (Z)-olefinic azlactones through a tandem Michael addition-ring transformation process has been developed. With DBU as the catalyst, a range of spiro-butyrolactoneoxindoles and spiro-butyrolactamoxindoles, containing an oxygen or a nitrogen heteroatom, respectively, in the spiro stereocenter, were smoothly obtained with good to excellent diastereoselectivities in high yields.
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.
Bao-Dong
BD
Cui
Jian
J
Zuo
Jian-Qiang
JQ
Zhao
Ming-Qiang
MQ
Zhou
Zhi-Jun
ZJ
Wu
Xiao-Mei
XM
Zhang
Wei-Cheng
WC
Yuan
D002384:Catalysis; D003500:Cyclization; D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003516:Cycloparaffins; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole