Brook/Elimination/Aldol Reaction (BEAR) Sequence for the Direct Preparation of Fluorinated Aldols from β,β‐Difluoro‐α‐(trimethylsilyl)alcohols | Zendy

Decostanzi Mélanie | Zendy; Van Der Lee Arie | Zendy; Campagne JeanMarc | Zendy; Leclerc Eric | Zendy

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Brook/Elimination/Aldol Reaction (BEAR) Sequence for the Direct Preparation of Fluorinated Aldols from β,β‐Difluoro‐α‐(trimethylsilyl)alcohols

Author(s) -

Decostanzi Mélanie,

Van Der Lee Arie,

Campagne JeanMarc,

Leclerc Eric

Publication year - 2015

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201500481

Subject(s) - aldol reaction , stereocenter , trimethylsilyl , chemistry , catalysis , sequence (biology) , fluoride , elimination reaction , base (topology) , stoichiometry , organic chemistry , enantioselective synthesis , inorganic chemistry , mathematical analysis , biochemistry , mathematics

A methodology allowing the preparation of aldols featuring a fluorinated stereogenic center is reported. The corresponding fluoroenolates are formed in situ from stable β,β‐difluoro‐α‐(trimethylsilyl)alcohols, through a base‐mediated process involving a Brook rearrangement followed by a fluoride elimination, and are directly added to aromatic aldehydes. Two different sets of conditions were disclosed. The first one involves the stoichiometric addition of potassium tert ‐butoxide ( t‐ BuOK) while the second is based on the use of a catalytic amount of an ammonium phenoxide. The latter opens the way for a catalytic and asymmetric version of this Brook/elimination/aldol reaction (BEAR) sequence.

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