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Gold‐Catalyzed One‐Step Construction of 2,3‐Dihydro‐1 H ‐Pyrrolizines with an Electron‐Withdrawing group in the 5‐position: A Formal Synthesis of 7‐Methoxymitosene
Author(s) -
Yan ZeYi,
Xiao Yuanjing,
Zhang Liming
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201203678
Subject(s) - regioselectivity , pericyclic reaction , polar effect , nitrene , azide , chemistry , ring (chemistry) , combinatorial chemistry , stereochemistry , position (finance) , catalysis , medicinal chemistry , organic chemistry , business , finance
What a ring formation! Bicyclic dihydropyrrolizines with an electron‐withdrawing group (EWG) at the 5‐position are formed in one step from linear azidoenynes under gold catalysis. This novel route involves the use of azide as a nitrene precursor, electronically‐controlled regioselectivity, and the generation of destabilized 1‐azapentadienium ions and their pericyclic reactions. This method was used for a formal synthesis of 7‐methoxymitosene (see scheme).