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Organocatalytic [3+2] Cycloadditions of Barbiturate‐Based Olefins with 3‐Isothiocyanato Oxindoles: Highly Diastereoselective and Enantioselective Synthesis of Dispirobarbiturates
Author(s) -
Zhao HongWu,
Tian Ting,
Pang HaiLiang,
Li Bo,
Chen XiaoQin,
Yang Zhao,
Meng Wei,
Song XiuQing,
Zhao YuDi,
Liu YueYang
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600270
Subject(s) - chemistry , enantioselective synthesis , cinchona , thiourea , catalysis , organocatalysis , organic chemistry , absolute configuration , barbiturate , combinatorial chemistry , psychology , psychiatry
Catalyzed by a Cinchona ‐based thiourea, the [3+2] cycloadditions of barbiturate‐based olefins with 3‐isothiocyanatooxindoles proceeded readily, and furnished dispirobarbiturates in excellent chemical yields with excellent diastereo‐ and enantioselectivities. The absolute configuration of dispirobarbiturates was firmly confirmed by an X‐ray single crystal structure analysis. A reaction mechanism was proposed to account for the enantioselective formation of dispirobarbiturates.