A Stereoselective Approach to Functionalized Cyclohexenones | Zendy

Meister Anne C. | Zendy; Sauter Paul F. | Zendy; Bräse Stefan | Zendy

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A Stereoselective Approach to Functionalized Cyclohexenones

Author(s) -

Meister Anne C.,

Sauter Paul F.,

Bräse Stefan

Publication year - 2013

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201300752

Subject(s) - chemistry , stereocenter , enantioselective synthesis , stereoselectivity , enantiomer , catalysis , enantiomeric excess , adduct , stereochemistry , ligand (biochemistry) , michael reaction , combinatorial chemistry , organic chemistry , biochemistry , receptor

A catalytic enantioselective approach to 4‐hydroxy‐6‐methylcyclohex‐2‐enones is presented herein. The stereogenic information is generated through a copper‐catalyzed 1,4‐addition to p ‐benzoquinone monoketal using a chiral, BINOL‐based (BINOL = 1,1′‐bi‐2‐naphthol) phosphane ligand, according to the procedure of Feringa et al. A CBS (Corey–Bakshi–Shibata) reduction of the 1,4‐adducts gave the four possible isomers in two steps and 82–97 % ee (enantiomeric excess), starting from commercially available 4,4‐dimethoxycyclohexa‐2,5‐dien‐1‐one ( 7 ).

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