Stereoselective 1,5-rearrangement of vinylketene-N,O-acetals: Novel vinylogous Ferrier reaction

Masaharu Inui; Seijiro Hosokawa; Atsuo Nakazaki; Susumu Kobayashi

doi:10.1016/j.tetlet.2005.03.050

Stereoselective 1,5-rearrangement of vinylketene-N,O-acetals: Novel vinylogous Ferrier reaction

Masaharu Inui, Seijiro Hosokawa, Atsuo Nakazaki, Susumu Kobayashi^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

11 Citations (Scopus)

Abstract

Vinylketene-N,O-acetals underwent Lewis acid-induced 1,3- or 1,5-rearrangement to afford the corresponding C-alkylated products. 1,5-Rearrangement proceeded predominantly in dichloromethane, and it is quite interesting to achieve an unprecedented high degree of asymmetric induction in such a remote position. Crossover experiments indicated that the reaction proceeded through an ion pair intermediate.

Original language	English
Pages (from-to)	3245-3248
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2005.03.050
Publication status	Published - 2005 May 2

Keywords

1,5-Rearrangement
Lewis acid
Vinylketene-N,O-acetal
Vinylogous Ferrier reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.03.050

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title = "Stereoselective 1,5-rearrangement of vinylketene-N,O-acetals: Novel vinylogous Ferrier reaction",

abstract = "Vinylketene-N,O-acetals underwent Lewis acid-induced 1,3- or 1,5-rearrangement to afford the corresponding C-alkylated products. 1,5-Rearrangement proceeded predominantly in dichloromethane, and it is quite interesting to achieve an unprecedented high degree of asymmetric induction in such a remote position. Crossover experiments indicated that the reaction proceeded through an ion pair intermediate.",

keywords = "1,5-Rearrangement, Lewis acid, Vinylketene-N,O-acetal, Vinylogous Ferrier reaction",

author = "Masaharu Inui and Seijiro Hosokawa and Atsuo Nakazaki and Susumu Kobayashi",

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T1 - Stereoselective 1,5-rearrangement of vinylketene-N,O-acetals

T2 - Novel vinylogous Ferrier reaction

AU - Inui, Masaharu

AU - Hosokawa, Seijiro

AU - Nakazaki, Atsuo

AU - Kobayashi, Susumu

PY - 2005/5/2

Y1 - 2005/5/2

N2 - Vinylketene-N,O-acetals underwent Lewis acid-induced 1,3- or 1,5-rearrangement to afford the corresponding C-alkylated products. 1,5-Rearrangement proceeded predominantly in dichloromethane, and it is quite interesting to achieve an unprecedented high degree of asymmetric induction in such a remote position. Crossover experiments indicated that the reaction proceeded through an ion pair intermediate.

AB - Vinylketene-N,O-acetals underwent Lewis acid-induced 1,3- or 1,5-rearrangement to afford the corresponding C-alkylated products. 1,5-Rearrangement proceeded predominantly in dichloromethane, and it is quite interesting to achieve an unprecedented high degree of asymmetric induction in such a remote position. Crossover experiments indicated that the reaction proceeded through an ion pair intermediate.

KW - 1,5-Rearrangement

KW - Lewis acid

KW - Vinylketene-N,O-acetal

KW - Vinylogous Ferrier reaction

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SN - 0040-4039

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EP - 3248

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

Stereoselective 1,5-rearrangement of vinylketene-N,O-acetals: Novel vinylogous Ferrier reaction

Abstract

Keywords

ASJC Scopus subject areas

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