Diastereoselective Temporary Silicon‐Tethered Ring‐Closing‐Metathesis Reactions with Prochiral Alcohols: A New Approach to Long‐Range Asymmetric Induction | Zendy

Evans P. Andrew | Zendy; Cui Jian | Zendy; Buffone Gerald P. | Zendy

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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.

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