Chelation control through the coordination of an olefinic π-bond to Lewis acid

N. Asao; T. Shimada; Y. Yamamoto

doi:10.1016/S0040-4039(00)01667-1

Chelation control through the coordination of an olefinic π-bond to Lewis acid

N. Asao, T. Shimada, Y. Yamamoto

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

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
Pages (from-to)	9533-9536
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4039(00)01667-1
Publication status	Published - 2000 Dec 2

Keywords

Alkenes
Allylation
Carbonyl compounds
Chelation
Lewis acid
Reduction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Chelation control through the coordination of an olefinic π-bond to Lewis acid",

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.",

keywords = "Alkenes, Allylation, Carbonyl compounds, Chelation, Lewis acid, Reduction",

author = "N. Asao and T. Shimada and Y. Yamamoto",

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doi = "10.1016/S0040-4039(00)01667-1",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Chelation control through the coordination of an olefinic π-bond to Lewis acid

AU - Asao, N.

AU - Shimada, T.

AU - Yamamoto, Y.

PY - 2000/12/2

Y1 - 2000/12/2

N2 - 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.

AB - 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.

KW - Alkenes

KW - Allylation

KW - Carbonyl compounds

KW - Chelation

KW - Lewis acid

KW - Reduction

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U2 - 10.1016/S0040-4039(00)01667-1

DO - 10.1016/S0040-4039(00)01667-1

M3 - Article

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VL - 41

SP - 9533

EP - 9536

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 49

ER -