Organic Letters 2012-06-15

Selective catalytic sp3 C-O bond cleavage with C-N bond formation in 3-alkoxy-1-propanols.

Cheng Chen, Soon Hyeok Hong

Index: Org. Lett. 14(12) , 2992-5, (2012)

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Abstract

The ruthenium catalyzed selective sp(3) C-O cleavage with amide formation was reported in reactions of 3-alkoxy-1-propanol derivatives and amines. The cleavage only occurs at the C3-O position even with 3-benzyloxy-1-propanol. Based on the experimental results, O-bound and C-bound Ru enolate complexes were proposed as key intermediates for the unique selective sp(3) C-O bond cleavage in 3-alkoxy-1-propanols.