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Enantioselective Synthesis of Spirooxindoles: Asymmetric [3+2] Cycloaddition of (3‐Isothiocyanato)oxindoles with Azodicarboxylates
Author(s) -
Jiang Yu,
Pei ChengKui,
Du Dan,
Li XiaoGe,
He YaNan,
Xu Qin,
Shi Min
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301418
Subject(s) - chemistry , oxindole , enantioselective synthesis , cycloaddition , catalysis , stereochemistry , combinatorial chemistry , organic chemistry
Abstract The catalytic asymmetric [3+2] cycloaddition of (3‐isothiocyanato)oxindoles with azodicarboxylates has been explored in the presence of (DHQD) 2 PHAL. It affords spirooxindoles having two heterocycles at their C3′‐position in excellent yields, with high enantioselectivities, and under mild conditions within 5 min. Moreover, another spirooxindole derived from the reaction of (3‐isothiocyanato)oxindole with two molecules of azodicarboxylate could also be formed in excellent yields with the same high enantioselectivities under the standard conditions.