Lewis Base Assisted Brønsted Base Catalysis: Direct Regioselective Asymmetric Vinylogous Alkylation of Allylic Sulfones | Zendy

Jiang Lin | Zendy; Lei Qian | Zendy; Huang Xin | Zendy; Cui HaiLei | Zendy; Zhou Xue | Zendy; Chen YingChun | Zendy

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Lewis Base Assisted Brønsted Base Catalysis: Direct Regioselective Asymmetric Vinylogous Alkylation of Allylic Sulfones

Author(s) -

Jiang Lin,

Lei Qian,

Huang Xin,

Cui HaiLei,

Zhou Xue,

Chen YingChun

Publication year - 2011

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201100534

Subject(s) - regioselectivity , tsuji–trost reaction , cinchona , chemistry , nucleophile , alkylation , lewis acids and bases , catalysis , enantiomer , organic chemistry , brønsted–lowry acid–base theory , dimethyl carbonate , medicinal chemistry , organocatalysis , enantiomeric excess , allylic rearrangement , enantioselective synthesis

A Lewis base assisted Brønsted base catalysis (LBABB) strategy is applied for direct asymmetric vinylogous alkylation of allylic sulfones with Morita–Baylis–Hillman (MBH) carbonates, in which a strong Brønsted base, tert ‐butoxy anion, generated in situ from a tertiary amine catalyst and MBH carbonate, is crucial in activating unstabilized nucleophiles. The γ‐regioselective alkylation products were obtained with good to excellent enantiomeric excess values when catalyzed by a modified cinchona alkaloid.

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