Environment friendly organic synthesis using bismuth compounds. An efficient method for carbonyl-ene reactions catalyzed by bismuth triflate

Erin D. Anderson; Justin J. Ernat; Mai P. Nguyen; Ann C. Palma; Ram S. Mohan

doi:10.1016/j.tetlet.2005.09.035

Environment friendly organic synthesis using bismuth compounds. An efficient method for carbonyl-ene reactions catalyzed by bismuth triflate

Erin D. Anderson, Justin J. Ernat, Mai P. Nguyen, Ann C. Palma, Ram S. Mohan

Orthopaedic Surgery

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

27 Scopus citations

Abstract

Bismuth triflate (0.1 mol %) is a highly efficient catalyst for the cyclization of citronellal 1, a reaction that yields a ratio of 80:20 of isopulegol 2 and neoisopulegol 3. This methodology has also been extended to the synthesis of substituted piperidines. The bismuth triflate catalyzed ene reaction of aldehyde 4 gives a 70:30 mixture of piperidines 5 and 6. The advantages of these methods include the use of a highly efficient catalyst that is relatively nontoxic, cheap and easy to handle.

Original language	English (US)
Pages (from-to)	7747-7750
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	45
DOIs	https://doi.org/10.1016/j.tetlet.2005.09.035
State	Published - Nov 7 2005

Bibliographical note

Funding Information:
We are grateful to the National Science Foundation for an RUI (Research at An Undergraduate Institution) grant. We also wish to acknowledge Research Corporation for a Cottrell College Science Award. R.M. wishes to thank The Camille and Henry Dreyfus Foundation for a Henry Dreyfus Teacher Scholar Award.

Keywords

Bismuth and compounds
Carbonyl-ene reaction
Cyclizations
Lewis acids

Publisher link

10.1016/j.tetlet.2005.09.035

Find It

Find It at U of M Libraries

Cite this

@article{0ebd896db6e1479b83c5f4d315fd1e68,

title = "Environment friendly organic synthesis using bismuth compounds. An efficient method for carbonyl-ene reactions catalyzed by bismuth triflate",

abstract = "Bismuth triflate (0.1 mol %) is a highly efficient catalyst for the cyclization of citronellal 1, a reaction that yields a ratio of 80:20 of isopulegol 2 and neoisopulegol 3. This methodology has also been extended to the synthesis of substituted piperidines. The bismuth triflate catalyzed ene reaction of aldehyde 4 gives a 70:30 mixture of piperidines 5 and 6. The advantages of these methods include the use of a highly efficient catalyst that is relatively nontoxic, cheap and easy to handle.",

keywords = "Bismuth and compounds, Carbonyl-ene reaction, Cyclizations, Lewis acids",

author = "Anderson, {Erin D.} and Ernat, {Justin J.} and Nguyen, {Mai P.} and Palma, {Ann C.} and Mohan, {Ram S.}",

note = "Funding Information: We are grateful to the National Science Foundation for an RUI (Research at An Undergraduate Institution) grant. We also wish to acknowledge Research Corporation for a Cottrell College Science Award. R.M. wishes to thank The Camille and Henry Dreyfus Foundation for a Henry Dreyfus Teacher Scholar Award. ",

year = "2005",

month = nov,

day = "7",

doi = "10.1016/j.tetlet.2005.09.035",

language = "English (US)",

volume = "46",

pages = "7747--7750",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "45",

}

TY - JOUR

T1 - Environment friendly organic synthesis using bismuth compounds. An efficient method for carbonyl-ene reactions catalyzed by bismuth triflate

AU - Anderson, Erin D.

AU - Ernat, Justin J.

AU - Nguyen, Mai P.

AU - Palma, Ann C.

AU - Mohan, Ram S.

N1 - Funding Information: We are grateful to the National Science Foundation for an RUI (Research at An Undergraduate Institution) grant. We also wish to acknowledge Research Corporation for a Cottrell College Science Award. R.M. wishes to thank The Camille and Henry Dreyfus Foundation for a Henry Dreyfus Teacher Scholar Award.

PY - 2005/11/7

Y1 - 2005/11/7

N2 - Bismuth triflate (0.1 mol %) is a highly efficient catalyst for the cyclization of citronellal 1, a reaction that yields a ratio of 80:20 of isopulegol 2 and neoisopulegol 3. This methodology has also been extended to the synthesis of substituted piperidines. The bismuth triflate catalyzed ene reaction of aldehyde 4 gives a 70:30 mixture of piperidines 5 and 6. The advantages of these methods include the use of a highly efficient catalyst that is relatively nontoxic, cheap and easy to handle.

AB - Bismuth triflate (0.1 mol %) is a highly efficient catalyst for the cyclization of citronellal 1, a reaction that yields a ratio of 80:20 of isopulegol 2 and neoisopulegol 3. This methodology has also been extended to the synthesis of substituted piperidines. The bismuth triflate catalyzed ene reaction of aldehyde 4 gives a 70:30 mixture of piperidines 5 and 6. The advantages of these methods include the use of a highly efficient catalyst that is relatively nontoxic, cheap and easy to handle.

KW - Bismuth and compounds

KW - Carbonyl-ene reaction

KW - Cyclizations

KW - Lewis acids

UR - http://www.scopus.com/inward/record.url?scp=26444524950&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=26444524950&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2005.09.035

DO - 10.1016/j.tetlet.2005.09.035

M3 - Article

AN - SCOPUS:26444524950

SN - 0040-4039

VL - 46

SP - 7747

EP - 7750

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

Environment friendly organic synthesis using bismuth compounds. An efficient method for carbonyl-ene reactions catalyzed by bismuth triflate

Abstract

Bibliographical note

Keywords

Publisher link

Find It

Other files and links

Fingerprint

Cite this