Abstract
(formula presented) A chiral bis(isoxazoline) ligand (SPRIX) containing a rigid spiro skeleton was designed and synthesized via a double intramolecular nitrile oxide cycloaddition. The optically pure SPRIX greatly accelerated the Cu(acac)2-catalyzed asymmetric reaction of diisopropylzinc with cyclohexenone to give the Michael adduct with 49% ee. This is the first example of the use of an isoxazoline ligand for a transition metal-catalyzed reaction. The X-ray crystallographic analysis of the hexacoordinated copper complex of SPRIX confirmed the ligand character.
Original language | English |
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Pages (from-to) | 1795-1797 |
Number of pages | 3 |
Journal | Organic Letters |
Volume | 1 |
Issue number | 11 |
DOIs | |
Publication status | Published - 1999 Dec 2 |
Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry