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

An Efficient Synthesis of (+)-Dihydromayurone

Eun Lee, Injae Shin, Tae Seong Kim

Research output: Contribution to journalArticle

45 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 languageEnglish
Pages (from-to)260-264
Number of pages5
JournalJournal of the American Chemical Society
Volume112
Issue number1
DOIs
Publication statusPublished - 1990 Jan 1

Fingerprint

Alcohols
Carbon
Chirality
Aldehydes
allyl alcohol

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

@article{869a911f638f47af9851d2ff34fd0d9c,
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 Injae Shin and Kim, {Tae Seong}",
year = "1990",
month = "1",
day = "1",
doi = "10.1021/ja00157a041",
language = "English",
volume = "112",
pages = "260--264",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "1",

}

TY - JOUR

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

T2 - An Efficient Synthesis of (+)-Dihydromayurone

AU - Lee, Eun

AU - Shin, Injae

AU - Kim, Tae Seong

PY - 1990/1/1

Y1 - 1990/1/1

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.

UR - http://www.scopus.com/inward/record.url?scp=0025270407&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0025270407&partnerID=8YFLogxK

U2 - 10.1021/ja00157a041

DO - 10.1021/ja00157a041

M3 - Article

VL - 112

SP - 260

EP - 264

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 1

ER -