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Organoytterbium Ate Complexes Extend the Value of Cyclobutenediones as Isoprene Equivalents
Author(s) -
Packard Emma,
Pascoe David D.,
Maddaluno Jacques,
Gonçalves Théo P.,
Harrowven David C.
Publication year - 2013
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.201307193
Subject(s) - synthon , isoprene , chemistry , electrophile , reactivity (psychology) , nucleophile , reagent , total synthesis , organic synthesis , combinatorial chemistry , organic chemistry , stereochemistry , medicine , polymer , alternative medicine , pathology , copolymer , catalysis
Changing course : While organolithium and Grignard reagents favor addition to C1 of A (R=Me), the corresponding organoytterbium reagents add to C2 (R= t Bu). Computational studies provide insights into the nature of organoytterbium species and their reactivity, and a total synthesis of (−)‐mansonone B illustrates the utility of the method in terpenoid synthesis. Tf=trifluoromethanesulfonyl.