Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: Metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2- dihydroxycyclohexane

Stephen G. Davies; Marcus J.C. Long; Andrew D. Smith

doi:10.1039/b509088a

Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: Metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2- dihydroxycyclohexane

Stephen G. Davies^*
, Marcus J.C. Long
, Andrew D. Smith

^*Corresponding author for this work

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

Abstract

Treatment of N,N-dibenzylaminocyclohex-2-ene with mCPBA in the presence of CCl₃CO₂H gives 1,2-anti-2,3-syn-1-trichloroacetoxy-2- hydroxy-3-N,N-dibenzylaminocyclohexane with high diastereoselectivity; this methodology has been used to facilitate the metal-free stereoselective syntheses of all the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane.

Original language	English
Pages (from-to)	4536-4538
Number of pages	3
Journal	Chemical Communications
Issue number	36
DOIs	https://doi.org/10.1039/b509088a
Publication status	Published - 28 Sept 2005

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@article{3ad6460408024903a9d9273e124f5562,

title = "Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: Metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2- dihydroxycyclohexane",

abstract = "Treatment of N,N-dibenzylaminocyclohex-2-ene with mCPBA in the presence of CCl3CO2H gives 1,2-anti-2,3-syn-1-trichloroacetoxy-2- hydroxy-3-N,N-dibenzylaminocyclohexane with high diastereoselectivity; this methodology has been used to facilitate the metal-free stereoselective syntheses of all the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane.",

author = "Davies, \{Stephen G.\} and Long, \{Marcus J.C.\} and Smith, \{Andrew D.\}",

year = "2005",

month = sep,

day = "28",

doi = "10.1039/b509088a",

language = "English",

pages = "4536--4538",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "36",

}

TY - JOUR

T1 - Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene

T2 - Metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2- dihydroxycyclohexane

AU - Davies, Stephen G.

AU - Long, Marcus J.C.

AU - Smith, Andrew D.

PY - 2005/9/28

Y1 - 2005/9/28

N2 - Treatment of N,N-dibenzylaminocyclohex-2-ene with mCPBA in the presence of CCl3CO2H gives 1,2-anti-2,3-syn-1-trichloroacetoxy-2- hydroxy-3-N,N-dibenzylaminocyclohexane with high diastereoselectivity; this methodology has been used to facilitate the metal-free stereoselective syntheses of all the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane.

AB - Treatment of N,N-dibenzylaminocyclohex-2-ene with mCPBA in the presence of CCl3CO2H gives 1,2-anti-2,3-syn-1-trichloroacetoxy-2- hydroxy-3-N,N-dibenzylaminocyclohexane with high diastereoselectivity; this methodology has been used to facilitate the metal-free stereoselective syntheses of all the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane.

UR - https://www.scopus.com/pages/publications/26444526175

U2 - 10.1039/b509088a

DO - 10.1039/b509088a

M3 - Article

AN - SCOPUS:26444526175

SN - 1359-7345

SP - 4536

EP - 4538

JO - Chemical Communications

JF - Chemical Communications

IS - 36

ER -

Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: Metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2- dihydroxycyclohexane

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