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Diverse Reactivity of Zirconacyclocumulenes Derived from Coupling of Benzynezirconocenes with 1,3‐Butadiynes towards Acyl Cyanides: Synthesis of Indeno[2,1‐ b ]pyrroles or [3]Cumulenones
Author(s) -
Fu Xiaoping,
Chen Jingjin,
Li Guangyu,
Liu Yuanhong
Publication year - 2009
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.200900951
Subject(s) - reactivity (psychology) , substituent , stereoselectivity , chemistry , cycloaddition , aryl , alkyl , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Versatility : Cycloaddition of carbamoyl cyanides to 1,3‐butadiynes via seven‐membered zirconacyclocumulenes yields dihydroindeno[2,1‐ b ]pyrroles (see scheme, right); a C(sp 2 )H bond on the aromatic substituent of the 1,3‐butadiyne reactant is activated in the process. In contrast, reactions with aryl or alkyl acyl cyanides provide a stereoselective route to cis ‐[3]cumulenones (left).