Abstract
Exposure of Morita-Baylis-Hillman (MBH) acetates to tertiary phosphine catalysts in the presence of 4,5-dichlorophthalimide enables regiospecific allylic substitution through a tandem SN2′-S N2′ mechanism. Through the use of the chiral phosphine catalyst (R)-Cl-MeO-BIPHEP, chiral racemic MBH acetate 4 is converted to the corresponding allylic amination product in 80% yield and 56% enantiomeric excess, thus establishing the feasibility of dynamic kinetic resolution.
Original language | English |
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Pages (from-to) | 1337-1339 |
Number of pages | 3 |
Journal | Organic Letters |
Volume | 6 |
Issue number | 8 |
DOIs | |
State | Published - 15 Apr 2004 |