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Diastereoselective Temporary Silicon‐Tethered Ring‐Closing‐Metathesis Reactions with Prochiral Alcohols: A New Approach to Long‐Range Asymmetric Induction
Author(s) -
Evans P. Andrew,
Cui Jian,
Buffone Gerald P.
Publication year - 2003
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.200250486
Subject(s) - ring closing metathesis , asymmetric induction , chemistry , metathesis , salt metathesis reaction , stereochemistry , ring (chemistry) , silicon , range (aeronautics) , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , materials science , composite material , polymerization , polymer
A useful approach to 1,4‐, 1,5‐, and 1,6‐stereocontrol, diastereoselective ring‐closing‐metathesis reactions that utilize temporary silicon tethers represent a new strategy for long‐range asymmetric induction. This method facilitates the construction of cis ‐1,4‐silaketals ( n =0, d.r.=20:1; see scheme), whereas the extension of this concept to higher alkenyl alcohols ( n =1–4) results in a reversal of diastereoselectivity that favors formation of the trans isomer.