Reactions of ketene silyl acetals with imine-complexes of titanium tetrachloride. New and convenient routes to 5,6-dihydro-2-pyridones and 5-amino-2-alkenoates

Stephan M. Brandstadter; Iwao Ojima; Kenji Herai

doi:10.1016/S0040-4039(00)95794-0

Reactions of ketene silyl acetals with imine-complexes of titanium tetrachloride. New and convenient routes to 5,6-dihydro-2-pyridones and 5-amino-2-alkenoates

Stephan M. Brandstadter
, Iwao Ojima
, Kenji Herai

Chemistry

Stony Brook University
Sagami Chemical Research Institute

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

40 Scopus citations

Abstract

The reactions of vinylketene silyl acetals (VKSAs) with imine complexes of TiCl₄ give the corresponding 5,6-dihydro-2-pyridones and/or 5-amino-2-alkenoates in good to excellent yields. It is suggested that an addition-cyclization mechanism is operative for the formation of 5,6-dihydro-2-pyridones in this formal cyclocondensation reaction.

Original language	English
Pages (from-to)	613-616
Number of pages	4
Journal	Tetrahedron Letters
Volume	28
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4039(00)95794-0
State	Published - 1987

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title = "Reactions of ketene silyl acetals with imine-complexes of titanium tetrachloride. New and convenient routes to 5,6-dihydro-2-pyridones and 5-amino-2-alkenoates",

abstract = "The reactions of vinylketene silyl acetals (VKSAs) with imine complexes of TiCl4 give the corresponding 5,6-dihydro-2-pyridones and/or 5-amino-2-alkenoates in good to excellent yields. It is suggested that an addition-cyclization mechanism is operative for the formation of 5,6-dihydro-2-pyridones in this formal cyclocondensation reaction.",

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year = "1987",

doi = "10.1016/S0040-4039(00)95794-0",

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pages = "613--616",

journal = "Tetrahedron Letters",

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T1 - Reactions of ketene silyl acetals with imine-complexes of titanium tetrachloride. New and convenient routes to 5,6-dihydro-2-pyridones and 5-amino-2-alkenoates

AU - Brandstadter, Stephan M.

AU - Ojima, Iwao

AU - Herai, Kenji

PY - 1987

Y1 - 1987

N2 - The reactions of vinylketene silyl acetals (VKSAs) with imine complexes of TiCl4 give the corresponding 5,6-dihydro-2-pyridones and/or 5-amino-2-alkenoates in good to excellent yields. It is suggested that an addition-cyclization mechanism is operative for the formation of 5,6-dihydro-2-pyridones in this formal cyclocondensation reaction.

AB - The reactions of vinylketene silyl acetals (VKSAs) with imine complexes of TiCl4 give the corresponding 5,6-dihydro-2-pyridones and/or 5-amino-2-alkenoates in good to excellent yields. It is suggested that an addition-cyclization mechanism is operative for the formation of 5,6-dihydro-2-pyridones in this formal cyclocondensation reaction.

UR - https://www.scopus.com/pages/publications/0000279109

U2 - 10.1016/S0040-4039(00)95794-0

DO - 10.1016/S0040-4039(00)95794-0

M3 - Article

AN - SCOPUS:0000279109

SN - 0040-4039

VL - 28

SP - 613

EP - 616

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

Reactions of ketene silyl acetals with imine-complexes of titanium tetrachloride. New and convenient routes to 5,6-dihydro-2-pyridones and 5-amino-2-alkenoates

Abstract

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