Acid‐Relayed Organocatalytic  exo ‐Diels–Alder Cycloaddition of Cyclic Enones with 2‐Vinyl‐1 H ‐indoles | Zendy

Ren JiWei | Zendy; Zhou ZhaoFang | Zendy; Xiao JunAn | Zendy; Chen XiaoQing | Zendy; Yang Hua | Zendy

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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 ).

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