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Enantiospecific Synthesis and Allylation of All‐Carbon‐Substituted α‐Chiral Allylic Stannanes
Author(s) -
Schmidtmann Eric S.,
Oestreich Martin
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.200901384
Subject(s) - allylic rearrangement , reagent , chemistry , lewis acids and bases , zinc , carbon fibers , enantiomer , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , materials science , composite number , composite material
Once difficult to obtain , the title compounds can be prepared in virtually enantiomerically pure form with a bis(triorganostannyl) zinc reagent (see scheme). Subsequent diastereoselective thermal (left) and Lewis acid promoted reactions (right) illustrate the synthetic potential of these compounds.