Sulfated zirconia (SO4/ZrO2) as a reusable solid acid catalyst for the Mannich-type reaction between ketene silyl acetals and aldimines

Sainan Wang; Shuichi Matsumura; Kazunobu Toshima

doi:10.1016/j.tetlet.2007.07.072

Sulfated zirconia (SO₄/ZrO₂) as a reusable solid acid catalyst for the Mannich-type reaction between ketene silyl acetals and aldimines

Sainan Wang, Shuichi Matsumura, Kazunobu Toshima

Department of Applied Chemistry

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

28 Citations (Scopus)

Abstract

Sulfated zirconia (SO₄/ZrO₂) catalyzed Mannich-type reactions of ketene silyl acetals and aldimines proceeded smoothly at room temperature to afford β-amino esters in good to high yields. In addition, the heterogeneous solid acid catalyst SO₄/ZrO₂ was easily recovered from the reaction mixture and then reused without significant loss of effectiveness.

Original language	English
Pages (from-to)	6449-6452
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2007.07.072
Publication status	Published - 2007 Sept 10

Keywords

Aldimine
Ketene silyl acetal
Mannich-type reaction
Solid acid
Sulfated zirconia

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2007.07.072

Cite this

@article{e1487ae74f08487599d843e63121cbda,

title = "Sulfated zirconia (SO4/ZrO2) as a reusable solid acid catalyst for the Mannich-type reaction between ketene silyl acetals and aldimines",

abstract = "Sulfated zirconia (SO4/ZrO2) catalyzed Mannich-type reactions of ketene silyl acetals and aldimines proceeded smoothly at room temperature to afford β-amino esters in good to high yields. In addition, the heterogeneous solid acid catalyst SO4/ZrO2 was easily recovered from the reaction mixture and then reused without significant loss of effectiveness.",

keywords = "Aldimine, Ketene silyl acetal, Mannich-type reaction, Solid acid, Sulfated zirconia",

author = "Sainan Wang and Shuichi Matsumura and Kazunobu Toshima",

note = "Funding Information: This research was supported in part by Grants-in-Aid from the 21st Century Century of Excellence (COE) Program {\textquoteleft}KEIO Life Conjugated Chemistry{\textquoteright} and from the Scientific Research on Priority Areas (No. 18032068) of the Ministry of Education, Culture, Sports, Science, and Technology of Japan.",

year = "2007",

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day = "10",

doi = "10.1016/j.tetlet.2007.07.072",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Sulfated zirconia (SO4/ZrO2) as a reusable solid acid catalyst for the Mannich-type reaction between ketene silyl acetals and aldimines

AU - Wang, Sainan

AU - Matsumura, Shuichi

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported in part by Grants-in-Aid from the 21st Century Century of Excellence (COE) Program ‘KEIO Life Conjugated Chemistry’ and from the Scientific Research on Priority Areas (No. 18032068) of the Ministry of Education, Culture, Sports, Science, and Technology of Japan.

PY - 2007/9/10

Y1 - 2007/9/10

N2 - Sulfated zirconia (SO4/ZrO2) catalyzed Mannich-type reactions of ketene silyl acetals and aldimines proceeded smoothly at room temperature to afford β-amino esters in good to high yields. In addition, the heterogeneous solid acid catalyst SO4/ZrO2 was easily recovered from the reaction mixture and then reused without significant loss of effectiveness.

AB - Sulfated zirconia (SO4/ZrO2) catalyzed Mannich-type reactions of ketene silyl acetals and aldimines proceeded smoothly at room temperature to afford β-amino esters in good to high yields. In addition, the heterogeneous solid acid catalyst SO4/ZrO2 was easily recovered from the reaction mixture and then reused without significant loss of effectiveness.

KW - Aldimine

KW - Ketene silyl acetal

KW - Mannich-type reaction

KW - Solid acid

KW - Sulfated zirconia

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