A simple, user-friendly process for the homologation of aldehydes using tosylhydrazone salts

VK Aggarwal; Javier Vicente-Fidalgo; B Pelotier; IP Holmes; Roger V. Bonnert

A simple, user-friendly process for the homologation of aldehydes using tosylhydrazone salts

VK Aggarwal^*, Javier Vicente-Fidalgo, B Pelotier, IP Holmes, Roger V. Bonnert

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

33 Citations (Scopus)

Abstract

Aldehydes can be homologated to ketones in moderate to good yields using aryldiazomethanes generated in situ from tosylhydrazones. Chiral aldehydes can be employed with almost complete retention of configuration. The tosylhydrazones can also be generated in situ from the corresponding aldehyde leading to a one-pot process for coupling two different carbonyl compounds to give ketones. (C) 2000 Elsevier Science Ltd. All rights reserved.

Translated title of the contribution	A simple, user-friendly process for the homologation of aldehydes using tosylhydrazone salts
Original language	English
Pages (from-to)	10327-10331
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	52
Publication status	Published - 23 Dec 2000

Keywords

ACID CATALYZED-REACTIONS
ETHYL DIAZOACETATE
AROMATIC-ALDEHYDES
TIN(II) CHLORIDE
ALPHA-ARYL
KETONES
ESTERS
CONVERSION

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@article{33a2dd2f330242ce8d2e29491a09e214,

title = "A simple, user-friendly process for the homologation of aldehydes using tosylhydrazone salts",

abstract = "Aldehydes can be homologated to ketones in moderate to good yields using aryldiazomethanes generated in situ from tosylhydrazones. Chiral aldehydes can be employed with almost complete retention of configuration. The tosylhydrazones can also be generated in situ from the corresponding aldehyde leading to a one-pot process for coupling two different carbonyl compounds to give ketones. (C) 2000 Elsevier Science Ltd. All rights reserved.",

keywords = "ACID CATALYZED-REACTIONS, ETHYL DIAZOACETATE, AROMATIC-ALDEHYDES, TIN(II) CHLORIDE, ALPHA-ARYL, KETONES, ESTERS, CONVERSION",

author = "VK Aggarwal and Javier Vicente-Fidalgo and B Pelotier and IP Holmes and Bonnert, {Roger V.}",

year = "2000",

month = dec,

day = "23",

language = "English",

volume = "41",

pages = "10327--10331",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "52",

}

TY - JOUR

T1 - A simple, user-friendly process for the homologation of aldehydes using tosylhydrazone salts

AU - Aggarwal, VK

AU - Vicente-Fidalgo, Javier

AU - Pelotier, B

AU - Holmes, IP

AU - Bonnert, Roger V.

PY - 2000/12/23

Y1 - 2000/12/23

N2 - Aldehydes can be homologated to ketones in moderate to good yields using aryldiazomethanes generated in situ from tosylhydrazones. Chiral aldehydes can be employed with almost complete retention of configuration. The tosylhydrazones can also be generated in situ from the corresponding aldehyde leading to a one-pot process for coupling two different carbonyl compounds to give ketones. (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - Aldehydes can be homologated to ketones in moderate to good yields using aryldiazomethanes generated in situ from tosylhydrazones. Chiral aldehydes can be employed with almost complete retention of configuration. The tosylhydrazones can also be generated in situ from the corresponding aldehyde leading to a one-pot process for coupling two different carbonyl compounds to give ketones. (C) 2000 Elsevier Science Ltd. All rights reserved.

KW - ACID CATALYZED-REACTIONS

KW - ETHYL DIAZOACETATE

KW - AROMATIC-ALDEHYDES

KW - TIN(II) CHLORIDE

KW - ALPHA-ARYL

KW - KETONES

KW - ESTERS

KW - CONVERSION

M3 - Article (Academic Journal)

SN - 0040-4039

VL - 41

SP - 10327

EP - 10331

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

A simple, user-friendly process for the homologation of aldehydes using tosylhydrazone salts

Abstract

Keywords

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