Regio‐ and Stereoselective [4+3] Cycloaddition Towards Fused 5,7,6‐Tricyclic Skeletons | Zendy

Gong Wanchun | Zendy; Liu Yun | Zendy; Zhang Jie | Zendy; Jiao Yingdong | Zendy; Xue Jijun | Zendy; Li Ying | Zendy

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Regio‐ and Stereoselective [4+3] Cycloaddition Towards Fused 5,7,6‐Tricyclic Skeletons

Author(s) -

Gong Wanchun,

Liu Yun,

Zhang Jie,

Jiao Yingdong,

Xue Jijun,

Li Ying

Publication year - 2013

Publication title -

chemistry – an asian journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.18

H-Index - 106

eISSN - 1861-471X

pISSN - 1861-4728

DOI - 10.1002/asia.201201066

Subject(s) - cycloaddition , furan , pyrrole , thiophene , chemistry , ring (chemistry) , tricyclic , stereoselectivity , allylic rearrangement , stereochemistry , combinatorial chemistry , computational chemistry , organic chemistry , catalysis

Ringer! Multi‐ring‐fused structures with 7‐membered carbocycles are often elusive because of 7‐membered ring strain and entropy. The [4+3] cycloaddition reaction between the allylic cation of a heterocyclic alcohol and a conjugated diene yields the 7‐membered ring of 5,7,6‐tricyclic structures. Skeletons with furan were constructed in the presence of Tf 2 O/2,6‐lutidine, while reactions with thiophene and pyrrole proceeded in the presence of Tf 2 O/2,6‐lutidine or ZnCl 2 .

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