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Enantiocontrolled Synthesis of (R)‐3‐Substituted Cyclohexanones Using (S)‐2‐(p‐Tolylsulfinyl)‐2‐cyclohexenone and Various Organometallic Reagents in 2,5‐Dimethyltetrahydrofuran
Author(s) -
Posner Gary H.,
Frye Leah L.
Publication year - 1984
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198400015
Subject(s) - chemistry , reagent , denticity , conjugate , enantiomer , chelation , cyclohexenone , solvent , group 2 organometallic chemistry , metal , organic chemistry , medicinal chemistry , molecule , mathematical analysis , mathematics
Four different ( R )‐3‐substituted cyclohexanones of 65–96% enantiomeric purity have been prepared in 58–84% yields via organometallic conjugate additions to ( S )‐2‐( p ‐tolylsulfinyl)cyclohexenone in 2,5‐dimethyltetrahydrofuran (DMTHF) as a solvent which allows more effective metal ion chelation by the bidentate β‐ketosulfoxide (and therefore higher asymmetric induction) than does THF. Several recently‐reported organotitanium reagents have been used effectively for the first time as Michael donors.