Stereoarrays with an All‐Carbon Quaternary Center: Diastereoselective Desymmetrization of Prochiral Malonaldehydes | Zendy

Linclau Bruno | Zendy; Cini Elena | Zendy; Oakes Catherine S. | Zendy; Josse Solen | Zendy; Light Mark | Zendy; Ironmonger Victoria | Zendy

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Stereoarrays with an All‐Carbon Quaternary Center: Diastereoselective Desymmetrization of Prochiral Malonaldehydes

Author(s) -

Linclau Bruno,

Cini Elena,

Oakes Catherine S.,

Josse Solen,

Light Mark,

Ironmonger Victoria

Publication year - 2012

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.201107370

Subject(s) - stereocenter , stannane , desymmetrization , nucleophile , chemistry , center (category theory) , chelation , stereochemistry , combinatorial chemistry , computer science , organic chemistry , enantioselective synthesis , catalysis , crystallography

Tamed by chelation : The MgBr 2 chelation of prochiral malonaldehydes allows diastereoselective monoaddition reactions with allyl stannane nucleophiles (see scheme; PG=protecting group, TBDMS= tert ‐butyldiphenylmethylsilyl, Tr=trityl). In the same pot, addition of a second nucleophile proceeds in high diastereoselectivity to generate nonsymmetric products with up to five contiguous stereogenic centers, including a chiral all‐carbon quaternary center.

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