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A Domino Sequence Consisting of Insertion, Coupling, Isomerization, and Diels–Alder Steps Yields Highly Fluorescent Spirocycles
Author(s) -
D'Souza Daniel M.,
Rominger Frank,
Müller Thomas J. J.
Publication year - 2004
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.200461489
Subject(s) - domino , isomerization , sequence (biology) , fluorescence , chemistry , coupling (piping) , combinatorial chemistry , organic chemistry , materials science , biochemistry , catalysis , physics , quantum mechanics , metallurgy
Four bonds at one stroke and products with intensive fluorescence result from a domino sequence consisting of insertion, coupling, isomerization, and Diels–Alder steps (see scheme, Ts=tosyl). Alkynoyl ortho ‐iodophenyl esters or N ‐(iodophenyl)alkynanilides 1 react with propargyl allyl ethers 2 to furnish spirocycles 3 .