Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation. A study in the correlation of the enol ether chain length and enantioselectivity

Benjamin F. Marcune; Sandor Karady; Paul J. Reider; Ross A. Miller; Mirlinda Biba; Lisa DiMichele; Robert A. Reamer

doi:10.1021/jo034854o

Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation. A study in the correlation of the enol ether chain length and enantioselectivity

Benjamin F. Marcune, Sandor Karady, Paul J. Reider, Ross A. Miller, Mirlinda Biba, Lisa DiMichele, Robert A. Reamer

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

29 Scopus citations

Abstract

The Sharpless asymmetric dihydroxylation reaction of enol ethers derived from their corresponding cyclic ketones, gave α-hydroxyketones with high enantioselectivity. The enantiomeric excess was found to be proportional to the length of the unbranched enol ether chain with a maximum ee for the pentyl enol ether. An efficient synthesis of α-hydroxy chromanone in >90% ee was demonstrated using this method.

Original language	English (US)
Pages (from-to)	8088-8091
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	68
Issue number	21
DOIs	https://doi.org/10.1021/jo034854o
State	Published - Oct 17 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo034854o

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Marcune, B. F., Karady, S., Reider, P. J., Miller, R. A., Biba, M., DiMichele, L., & Reamer, R. A. (2003). Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation. A study in the correlation of the enol ether chain length and enantioselectivity. Journal of Organic Chemistry, 68(21), 8088-8091. https://doi.org/10.1021/jo034854o

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title = "Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation. A study in the correlation of the enol ether chain length and enantioselectivity",

abstract = "The Sharpless asymmetric dihydroxylation reaction of enol ethers derived from their corresponding cyclic ketones, gave α-hydroxyketones with high enantioselectivity. The enantiomeric excess was found to be proportional to the length of the unbranched enol ether chain with a maximum ee for the pentyl enol ether. An efficient synthesis of α-hydroxy chromanone in >90% ee was demonstrated using this method.",

author = "Marcune, {Benjamin F.} and Sandor Karady and Reider, {Paul J.} and Miller, {Ross A.} and Mirlinda Biba and Lisa DiMichele and Reamer, {Robert A.}",

year = "2003",

month = oct,

day = "17",

doi = "10.1021/jo034854o",

language = "English (US)",

volume = "68",

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Marcune, BF, Karady, S, Reider, PJ, Miller, RA, Biba, M, DiMichele, L & Reamer, RA 2003, 'Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation. A study in the correlation of the enol ether chain length and enantioselectivity', Journal of Organic Chemistry, vol. 68, no. 21, pp. 8088-8091. https://doi.org/10.1021/jo034854o

Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation. A study in the correlation of the enol ether chain length and enantioselectivity. / Marcune, Benjamin F.; Karady, Sandor; Reider, Paul J. et al.
In: Journal of Organic Chemistry, Vol. 68, No. 21, 17.10.2003, p. 8088-8091.

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

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T1 - Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation. A study in the correlation of the enol ether chain length and enantioselectivity

AU - Marcune, Benjamin F.

AU - Karady, Sandor

AU - Reider, Paul J.

AU - Miller, Ross A.

AU - Biba, Mirlinda

AU - DiMichele, Lisa

AU - Reamer, Robert A.

PY - 2003/10/17

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N2 - The Sharpless asymmetric dihydroxylation reaction of enol ethers derived from their corresponding cyclic ketones, gave α-hydroxyketones with high enantioselectivity. The enantiomeric excess was found to be proportional to the length of the unbranched enol ether chain with a maximum ee for the pentyl enol ether. An efficient synthesis of α-hydroxy chromanone in >90% ee was demonstrated using this method.

AB - The Sharpless asymmetric dihydroxylation reaction of enol ethers derived from their corresponding cyclic ketones, gave α-hydroxyketones with high enantioselectivity. The enantiomeric excess was found to be proportional to the length of the unbranched enol ether chain with a maximum ee for the pentyl enol ether. An efficient synthesis of α-hydroxy chromanone in >90% ee was demonstrated using this method.

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Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation. A study in the correlation of the enol ether chain length and enantioselectivity

Abstract

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