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Acid‐Relayed Organocatalytic exo ‐Diels–Alder Cycloaddition of Cyclic Enones with 2‐Vinyl‐1 H ‐indoles
Author(s) -
Ren JiWei,
Zhou ZhaoFang,
Xiao JunAn,
Chen XiaoQing,
Yang Hua
Publication year - 2016
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.201501619
Subject(s) - chemistry , stereocenter , cycloaddition , enantioselective synthesis , diels–alder reaction , hydrogen bond , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis , molecule
With the aid of the hydrogen‐bond relay of ( S )‐camphorsulfonic acid, the enantioselective exo ‐Diels–Alder cycloaddition of cyclic enones and 2‐vinyl‐1 H ‐indoles catalyzed by prolinosulfonamide was developed. The corresponding Diels–Alder cycloadducts were readily obtained by a single recrystallization, free of column chromatography. Consequently, tetracyclic tetrahydrocarbazole ring systems with three contiguous stereogenic centers were prepared in moderate yields with excellent diastereoselectivities ( exo / endo up to >20:1) and enantioselectivities (up to > 99 % ee ).