Tandem oxidation processes for the preparation of functionalized cyclopropanes

M F  Oswald; S A  Raw; R J K  Taylor

Tandem oxidation processes for the preparation of functionalized cyclopropanes

M F Oswald, S A Raw, R J K Taylor

Chemistry

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

Abstract

A novel manganese dioxide-mediated tandem oxidation process (TOP) has been developed which allows the direct conversion of allylic alcohols into cyclopropanes, the intermediate aldehydes being trapped in situ with a stabilized sulfur-ylide. This methodology has been applied successfully to a variety of allylic alcohols and to a formal synthesis of the simple, naturally occurring lignan, (+/-)-picropodophyllone.

Original language	English
Pages (from-to)	3997-4000
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	22
Publication status	Published - 28 Oct 2004

Keywords

ETHYL (DIMETHYLSULFURANYLIDENE)ACETATE
ALCOHOLS
MECHANISM
REDUCTION
ALDEHYDES
YLIDES
SCOPE

Cite this

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title = "Tandem oxidation processes for the preparation of functionalized cyclopropanes",

abstract = "A novel manganese dioxide-mediated tandem oxidation process (TOP) has been developed which allows the direct conversion of allylic alcohols into cyclopropanes, the intermediate aldehydes being trapped in situ with a stabilized sulfur-ylide. This methodology has been applied successfully to a variety of allylic alcohols and to a formal synthesis of the simple, naturally occurring lignan, (+/-)-picropodophyllone.",

keywords = "ETHYL (DIMETHYLSULFURANYLIDENE)ACETATE, ALCOHOLS, MECHANISM, REDUCTION, ALDEHYDES, YLIDES, SCOPE",

author = "Oswald, {M F} and Raw, {S A} and Taylor, {R J K}",

year = "2004",

month = oct,

day = "28",

language = "English",

volume = "6",

pages = "3997--4000",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Tandem oxidation processes for the preparation of functionalized cyclopropanes

AU - Oswald, M F

AU - Raw, S A

AU - Taylor, R J K

PY - 2004/10/28

Y1 - 2004/10/28

N2 - A novel manganese dioxide-mediated tandem oxidation process (TOP) has been developed which allows the direct conversion of allylic alcohols into cyclopropanes, the intermediate aldehydes being trapped in situ with a stabilized sulfur-ylide. This methodology has been applied successfully to a variety of allylic alcohols and to a formal synthesis of the simple, naturally occurring lignan, (+/-)-picropodophyllone.

AB - A novel manganese dioxide-mediated tandem oxidation process (TOP) has been developed which allows the direct conversion of allylic alcohols into cyclopropanes, the intermediate aldehydes being trapped in situ with a stabilized sulfur-ylide. This methodology has been applied successfully to a variety of allylic alcohols and to a formal synthesis of the simple, naturally occurring lignan, (+/-)-picropodophyllone.

KW - ETHYL (DIMETHYLSULFURANYLIDENE)ACETATE

KW - ALCOHOLS

KW - MECHANISM

KW - REDUCTION

KW - ALDEHYDES

KW - YLIDES

KW - SCOPE

M3 - Article

SN - 1523-7060

VL - 6

SP - 3997

EP - 4000

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -