Tetrahedron p. 7753 - 7776 (1997)
Update date:2022-08-04
Topics: Synthesis Epoxidation Metalloporphyrins Catalytic Terpene-derived D4-symmetric
Barry, John F.
Campbell, Lara
Smith, Dudley W.
Kodadek, Thomas
We report here a flexible synthesis of chiral, D4-symmetric porphyrins from cyclic ketone starting materials. Two porphyrins have been synthesized from the terpene 1-R-(+)-nopinone, obviating the need to perform a resolution. The chloromanganese derivative of one of these porphyrins is a good catalyst for the epoxidation of terminal alkenes, providing epoxides with e.e.'s of 70% with high turnover numbers. A predictive model for oxygen atom transfer in the chiral pocket is discussed.
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