Abstract
The reaction of a 1:1 mixture of ortho-alkenylbenzaldehydes 3 and their para-isomers 4 with Bu3SnH (1 equiv.) in the presence of Me3Al (1 equiv.) resulted in very high (>10:1) to good (3.4:1) chemoselective reduction of 3, giving the ortho-alkenyl benzyl alcohol 5 selectively. Similarly, the highly chemoselective allylation of 3d in the presence of 4d was observed when the mixture was treated with allyltributyltin/Me3Al. The chemoselectivities are most probably due to the bidentate chelation of the Lewis acid to an olefinic π-bond and a lone pair of aldehydes. (C) 2000 Published by Elsevier Science Ltd.
Original language | English |
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Pages (from-to) | 9533-9536 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 41 |
Issue number | 49 |
DOIs | |
Publication status | Published - 2000 Dec 2 |
Keywords
- Alkenes
- Allylation
- Carbonyl compounds
- Chelation
- Lewis acid
- Reduction
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry