Enantiocontrolled Synthesis of Quaternary Carbon Centers via Anionic Oxy-Cope Rearrangement: An Efficient Synthesis of (+)-Dihydromayurone

Eun Lee; In Jae Shin; Tae Seong Kim

doi:10.1021/ja00157a041

Enantiocontrolled Synthesis of Quaternary Carbon Centers via Anionic Oxy-Cope Rearrangement: An Efficient Synthesis of (+)-Dihydromayurone

Eun Lee, In Jae Shin, Tae Seong Kim

Department of Chemistry

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

46 Citations (Scopus)

Abstract

(+)-Dihydromayurone (1) was enantioselectively synthesized from β-cyclocitral (7). The key step in the synthesis involved anionic oxy-Cope rearrangement of allylic alcohol 6 to aldehyde 5. Efficient transfer of chirality from the secondary allylic alcohol center to the quaternary carbon center was observed via chairlike transition state with the equatorial oxyanionic bond.

Original language	English
Pages (from-to)	260-264
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	112
Issue number	1
DOIs	https://doi.org/10.1021/ja00157a041
Publication status	Published - 1990

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00157a041

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title = "Enantiocontrolled Synthesis of Quaternary Carbon Centers via Anionic Oxy-Cope Rearrangement: An Efficient Synthesis of (+)-Dihydromayurone",

abstract = "(+)-Dihydromayurone (1) was enantioselectively synthesized from β-cyclocitral (7). The key step in the synthesis involved anionic oxy-Cope rearrangement of allylic alcohol 6 to aldehyde 5. Efficient transfer of chirality from the secondary allylic alcohol center to the quaternary carbon center was observed via chairlike transition state with the equatorial oxyanionic bond.",

author = "Eun Lee and Shin, {In Jae} and Kim, {Tae Seong}",

year = "1990",

doi = "10.1021/ja00157a041",

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volume = "112",

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journal = "Journal of the American Chemical Society",

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T1 - Enantiocontrolled Synthesis of Quaternary Carbon Centers via Anionic Oxy-Cope Rearrangement

T2 - An Efficient Synthesis of (+)-Dihydromayurone

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AU - Shin, In Jae

AU - Kim, Tae Seong

PY - 1990

Y1 - 1990

N2 - (+)-Dihydromayurone (1) was enantioselectively synthesized from β-cyclocitral (7). The key step in the synthesis involved anionic oxy-Cope rearrangement of allylic alcohol 6 to aldehyde 5. Efficient transfer of chirality from the secondary allylic alcohol center to the quaternary carbon center was observed via chairlike transition state with the equatorial oxyanionic bond.

AB - (+)-Dihydromayurone (1) was enantioselectively synthesized from β-cyclocitral (7). The key step in the synthesis involved anionic oxy-Cope rearrangement of allylic alcohol 6 to aldehyde 5. Efficient transfer of chirality from the secondary allylic alcohol center to the quaternary carbon center was observed via chairlike transition state with the equatorial oxyanionic bond.

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Enantiocontrolled Synthesis of Quaternary Carbon Centers via Anionic Oxy-Cope Rearrangement: An Efficient Synthesis of (+)-Dihydromayurone

Abstract

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