Highly Diastereoselective Construction of Acyclic Systems with Two Adjacent Quaternary Stereocenters by Allylation of Ketones | Zendy

Takeda Takeshi | Zendy; Yamamoto Masanori | Zendy; Yoshida Satoshi | Zendy; Tsubouchi Akira | Zendy

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Highly Diastereoselective Construction of Acyclic Systems with Two Adjacent Quaternary Stereocenters by Allylation of Ketones

Author(s) -

Takeda Takeshi,

Yamamoto Masanori,

Yoshida Satoshi,

Tsubouchi Akira

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.201202808

Subject(s) - stereocenter , allylic rearrangement , stereospecificity , chemistry , group (periodic table) , stereochemistry , quaternary carbon , medicinal chemistry , catalysis , organic chemistry , enantioselective synthesis

Unsymmetrical ketones and allyltitanocenes generated by the desulfurizative titanation of γ,γ‐disubstituted allyl phenyl sulfides react under highly diastereoselective construction of adjacent quaternary stereocenters (see scheme; R L =large group, R S =small group). The title reaction is stereospecific: the anti ‐ and syn ‐homoallylic alcohols are obtained by the reaction of E ‐ and Z ‐allylic sulfides, respectively.

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