Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones: Asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps

Michael Palucki; Joann M. Um; Nobuyoshi Yasuda; David A. Conlon; Fuh Rong Tsay; Frederick W. Hartner; Yi Hsiao; Benjamin Marcune; Sandor Karady; David L. Hughes; Peter G. Dormer; Paul J. Reider

doi:10.1021/jo025890a

Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones: Asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps

Michael Palucki, Joann M. Um, Nobuyoshi Yasuda, David A. Conlon, Fuh Rong Tsay, Frederick W. Hartner, Yi Hsiao, Benjamin Marcune, Sandor Karady, David L. Hughes, Peter G. Dormer, Paul J. Reider

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

32 Scopus citations

Abstract

An efficient and practical asymmetric synthesis of (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)-cyclopentanone (1) is described. An asymmetric Mo-catalyzed alkylation reaction was used to establish the first stereocenter and a Cu-catalyzed intramolecular diastereoselective cyclopropanation reaction was used to set the second stereocenter. The last step involved a one-pot ring-opening/deprotection/hydrolysis/decarboxylation sequence that furnished the desired product in good yield.

Original language	English (US)
Pages (from-to)	5508-5516
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	67
Issue number	16
DOIs	https://doi.org/10.1021/jo025890a
State	Published - Aug 9 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo025890a

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Palucki, M., Um, J. M., Yasuda, N., Conlon, D. A., Tsay, F. R., Hartner, F. W., Hsiao, Y., Marcune, B., Karady, S., Hughes, D. L., Dormer, P. G., & Reider, P. J. (2002). Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones: Asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps. Journal of Organic Chemistry, 67(16), 5508-5516. https://doi.org/10.1021/jo025890a

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title = "Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones: Asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps",

abstract = "An efficient and practical asymmetric synthesis of (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)-cyclopentanone (1) is described. An asymmetric Mo-catalyzed alkylation reaction was used to establish the first stereocenter and a Cu-catalyzed intramolecular diastereoselective cyclopropanation reaction was used to set the second stereocenter. The last step involved a one-pot ring-opening/deprotection/hydrolysis/decarboxylation sequence that furnished the desired product in good yield.",

author = "Michael Palucki and Um, \{Joann M.\} and Nobuyoshi Yasuda and Conlon, \{David A.\} and Tsay, \{Fuh Rong\} and Hartner, \{Frederick W.\} and Yi Hsiao and Benjamin Marcune and Sandor Karady and Hughes, \{David L.\} and Dormer, \{Peter G.\} and Reider, \{Paul J.\}",

year = "2002",

month = aug,

day = "9",

doi = "10.1021/jo025890a",

language = "English (US)",

volume = "67",

pages = "5508--5516",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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Palucki, M, Um, JM, Yasuda, N, Conlon, DA, Tsay, FR, Hartner, FW, Hsiao, Y, Marcune, B, Karady, S, Hughes, DL, Dormer, PG & Reider, PJ 2002, 'Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones: Asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps', Journal of Organic Chemistry, vol. 67, no. 16, pp. 5508-5516. https://doi.org/10.1021/jo025890a

Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones: Asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps. / Palucki, Michael; Um, Joann M.; Yasuda, Nobuyoshi et al.
In: Journal of Organic Chemistry, Vol. 67, No. 16, 09.08.2002, p. 5508-5516.

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

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T1 - Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones

T2 - Asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps

AU - Palucki, Michael

AU - Um, Joann M.

AU - Yasuda, Nobuyoshi

AU - Conlon, David A.

AU - Tsay, Fuh Rong

AU - Hartner, Frederick W.

AU - Hsiao, Yi

AU - Marcune, Benjamin

AU - Karady, Sandor

AU - Hughes, David L.

AU - Dormer, Peter G.

AU - Reider, Paul J.

PY - 2002/8/9

Y1 - 2002/8/9

N2 - An efficient and practical asymmetric synthesis of (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)-cyclopentanone (1) is described. An asymmetric Mo-catalyzed alkylation reaction was used to establish the first stereocenter and a Cu-catalyzed intramolecular diastereoselective cyclopropanation reaction was used to set the second stereocenter. The last step involved a one-pot ring-opening/deprotection/hydrolysis/decarboxylation sequence that furnished the desired product in good yield.

AB - An efficient and practical asymmetric synthesis of (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)-cyclopentanone (1) is described. An asymmetric Mo-catalyzed alkylation reaction was used to establish the first stereocenter and a Cu-catalyzed intramolecular diastereoselective cyclopropanation reaction was used to set the second stereocenter. The last step involved a one-pot ring-opening/deprotection/hydrolysis/decarboxylation sequence that furnished the desired product in good yield.

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Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones: Asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps

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