Synthesis of alpha-hydroxy ketones from terpene aldehydes

M  Schueler; H  Zorn; A M Z  Slawin; R G  Berger

doi:10.1081/SCC-200025618

Synthesis of alpha-hydroxy ketones from terpene aldehydes

M Schueler, H Zorn, A M Z Slawin, R G Berger

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

Abstract

Unsymmetrically substituted alpha-hydroxy ketones possessing isoprenoid units within the molecule were synthesised from commercially available terpene aldehydes. The synthesis was applicable to alpha,beta-unsaturated aldehydes and afforded the respective a-hydroxy-methyl ketones in overall good yield. Tautomerisation of these products did not occur under the conditions of reaction but was observed upon heating. Diastereoisomeric alpha-hydroxy ketones have been resolved, and X-ray analysis on one of these analogues allowed for the elucidation of the stereochemistry after conversion into its camphanate ester.

Original language	English
Pages (from-to)	2591-2600
Number of pages	10
Journal	Synthetic Communications
Volume	34
Issue number	14
DOIs	https://doi.org/10.1081/SCC-200025618
Publication status	Published - Jul 2004

Keywords

acyloins
alpha-hydroxy ketones
terpene aldehydes
cyanohydrin trimethylsilyl ethers
copper salt catalysis
nitriles
Grignard reaction
camphanates
tautomerisation
CYANOHYDRINS
BUTANOLIDES
KETIMINES
NITRILES
REAGENTS
AMINES

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10.1081/SCC-200025618

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title = "Synthesis of alpha-hydroxy ketones from terpene aldehydes",

abstract = "Unsymmetrically substituted alpha-hydroxy ketones possessing isoprenoid units within the molecule were synthesised from commercially available terpene aldehydes. The synthesis was applicable to alpha,beta-unsaturated aldehydes and afforded the respective a-hydroxy-methyl ketones in overall good yield. Tautomerisation of these products did not occur under the conditions of reaction but was observed upon heating. Diastereoisomeric alpha-hydroxy ketones have been resolved, and X-ray analysis on one of these analogues allowed for the elucidation of the stereochemistry after conversion into its camphanate ester.",

keywords = "acyloins, alpha-hydroxy ketones, terpene aldehydes, cyanohydrin trimethylsilyl ethers, copper salt catalysis, nitriles, Grignard reaction, camphanates, tautomerisation, CYANOHYDRINS, BUTANOLIDES, KETIMINES, NITRILES, REAGENTS, AMINES",

author = "M Schueler and H Zorn and Slawin, {A M Z} and Berger, {R G}",

year = "2004",

month = jul,

doi = "10.1081/SCC-200025618",

language = "English",

volume = "34",

pages = "2591--2600",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis",

number = "14",

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TY - JOUR

T1 - Synthesis of alpha-hydroxy ketones from terpene aldehydes

AU - Schueler, M

AU - Zorn, H

AU - Slawin, A M Z

AU - Berger, R G

PY - 2004/7

Y1 - 2004/7

N2 - Unsymmetrically substituted alpha-hydroxy ketones possessing isoprenoid units within the molecule were synthesised from commercially available terpene aldehydes. The synthesis was applicable to alpha,beta-unsaturated aldehydes and afforded the respective a-hydroxy-methyl ketones in overall good yield. Tautomerisation of these products did not occur under the conditions of reaction but was observed upon heating. Diastereoisomeric alpha-hydroxy ketones have been resolved, and X-ray analysis on one of these analogues allowed for the elucidation of the stereochemistry after conversion into its camphanate ester.

AB - Unsymmetrically substituted alpha-hydroxy ketones possessing isoprenoid units within the molecule were synthesised from commercially available terpene aldehydes. The synthesis was applicable to alpha,beta-unsaturated aldehydes and afforded the respective a-hydroxy-methyl ketones in overall good yield. Tautomerisation of these products did not occur under the conditions of reaction but was observed upon heating. Diastereoisomeric alpha-hydroxy ketones have been resolved, and X-ray analysis on one of these analogues allowed for the elucidation of the stereochemistry after conversion into its camphanate ester.

KW - acyloins

KW - alpha-hydroxy ketones

KW - terpene aldehydes

KW - cyanohydrin trimethylsilyl ethers

KW - copper salt catalysis

KW - nitriles

KW - Grignard reaction

KW - camphanates

KW - tautomerisation

KW - CYANOHYDRINS

KW - BUTANOLIDES

KW - KETIMINES

KW - NITRILES

KW - REAGENTS

KW - AMINES

UR - http://www.scopus.com/inward/record.url?scp=3843092611&partnerID=8YFLogxK

U2 - 10.1081/SCC-200025618

DO - 10.1081/SCC-200025618

M3 - Article

SN - 0039-7911

VL - 34

SP - 2591

EP - 2600

JO - Synthetic Communications

JF - Synthetic Communications

IS - 14

ER -

Synthesis of alpha-hydroxy ketones from terpene aldehydes

Abstract

Keywords

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