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

33 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",

pages = "8088--8091",

journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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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

TY - JOUR

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

Y1 - 2003/10/17

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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JF - Journal of Organic Chemistry

IS - 21

ER -

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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