Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol

Caroline Aciro; Stephen G. Davies; Paul M. Roberts; Angela J. Russell; Andrew D. Smith; James E. Thomson

doi:10.1039/b808812h

Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol

Caroline Aciro, Stephen G. Davies, Paul M. Roberts, Angela J. Russell, Andrew D. Smith, James E. Thomson

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

Abstract

The ammonium-directed, metal-free oxidation of 3-(N,N-dibenzylamino)cyclohex-1-ene with mCPBA in the presence of either trichloroacetic acid or tosic acid has been used as the key step to facilitate the synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol, in >98% de in each case.

Original language	English
Pages (from-to)	3762-3770
Number of pages	9
Journal	Organic & Biomolecular Chemistry
Volume	6
Issue number	20
DOIs	https://doi.org/10.1039/b808812h
Publication status	Published - 21 Oct 2008

Keywords

JASPINE-B PACHASTRISSAMINE
D-LYXO-PHYTOSPHINGOSINE
VICINAL AMINO-ALCOHOLS
ASYMMETRIC-SYNTHESIS
STEREOSELECTIVE EPOXIDATION
MECHANISMS
SALTS

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title = "Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol",

abstract = "The ammonium-directed, metal-free oxidation of 3-(N,N-dibenzylamino)cyclohex-1-ene with mCPBA in the presence of either trichloroacetic acid or tosic acid has been used as the key step to facilitate the synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol, in >98% de in each case.",

keywords = "JASPINE-B PACHASTRISSAMINE, D-LYXO-PHYTOSPHINGOSINE, VICINAL AMINO-ALCOHOLS, ASYMMETRIC-SYNTHESIS, STEREOSELECTIVE EPOXIDATION, MECHANISMS, SALTS",

author = "Caroline Aciro and Davies, {Stephen G.} and Roberts, {Paul M.} and Russell, {Angela J.} and Smith, {Andrew D.} and Thomson, {James E.}",

year = "2008",

month = oct,

day = "21",

doi = "10.1039/b808812h",

language = "English",

volume = "6",

pages = "3762--3770",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0539",

publisher = "Royal Society of Chemistry",

number = "20",

}

TY - JOUR

T1 - Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol

AU - Aciro, Caroline

AU - Davies, Stephen G.

AU - Roberts, Paul M.

AU - Russell, Angela J.

AU - Smith, Andrew D.

AU - Thomson, James E.

PY - 2008/10/21

Y1 - 2008/10/21

N2 - The ammonium-directed, metal-free oxidation of 3-(N,N-dibenzylamino)cyclohex-1-ene with mCPBA in the presence of either trichloroacetic acid or tosic acid has been used as the key step to facilitate the synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol, in >98% de in each case.

AB - The ammonium-directed, metal-free oxidation of 3-(N,N-dibenzylamino)cyclohex-1-ene with mCPBA in the presence of either trichloroacetic acid or tosic acid has been used as the key step to facilitate the synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol, in >98% de in each case.

KW - JASPINE-B PACHASTRISSAMINE

KW - D-LYXO-PHYTOSPHINGOSINE

KW - VICINAL AMINO-ALCOHOLS

KW - ASYMMETRIC-SYNTHESIS

KW - STEREOSELECTIVE EPOXIDATION

KW - MECHANISMS

KW - SALTS

U2 - 10.1039/b808812h

DO - 10.1039/b808812h

M3 - Article

SN - 1477-0539

VL - 6

SP - 3762

EP - 3770

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 20

ER -

Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol

Abstract

Keywords

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