Regioselective asymmetric aminohydroxylation of precursors to 2,3,6- trideoxy-3-aminohexoses

Roger M. Davey; Margaret A. Brimble; Malcolm D. McLeod

doi:10.1016/S0040-4039(00)00798-X

Regioselective asymmetric aminohydroxylation of precursors to 2,3,6- trideoxy-3-aminohexoses

Roger M. Davey, Margaret A. Brimble^*, Malcolm D. McLeod

^*Corresponding author for this work

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

17 Citations (Scopus)

Abstract

The catalytic asymmetric aminohydroxylation (AA) of 5-substituted-pent- 2-enoates 8 and 17 was investigated as a route to 2,3,6-trideoxy-3- aminohexoses. The AA of ester 8, which bears a dimethyl acetal at C-5, favoured formation of the α-amino regioisomer 11 with optimum regioselectivity being observed using (DHQ)₂AQN as the chiral ligand and the chloramine salt of ethyl carbamate as the nitrogen source. Ester 17, which has a 4-methoxyphenoxy group at C-5, undergoes highly regioselective AA affording the β-amino regioisomer 19 in excellent enantiomeric excess, thereby establishing that introduction of this aromatic group leads to a superior substrate for AA. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	5141-5145
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4039(00)00798-X
Publication status	Published - 24 Jun 2000
Externally published	Yes

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title = "Regioselective asymmetric aminohydroxylation of precursors to 2,3,6- trideoxy-3-aminohexoses",

abstract = "The catalytic asymmetric aminohydroxylation (AA) of 5-substituted-pent- 2-enoates 8 and 17 was investigated as a route to 2,3,6-trideoxy-3- aminohexoses. The AA of ester 8, which bears a dimethyl acetal at C-5, favoured formation of the α-amino regioisomer 11 with optimum regioselectivity being observed using (DHQ)2AQN as the chiral ligand and the chloramine salt of ethyl carbamate as the nitrogen source. Ester 17, which has a 4-methoxyphenoxy group at C-5, undergoes highly regioselective AA affording the β-amino regioisomer 19 in excellent enantiomeric excess, thereby establishing that introduction of this aromatic group leads to a superior substrate for AA. (C) 2000 Elsevier Science Ltd.",

keywords = "Amino alcohols, Asymmetric aminohydroxylation, Asymmetric catalysis, Asymmetric synthesis, Osmium",

author = "Davey, {Roger M.} and Brimble, {Margaret A.} and McLeod, {Malcolm D.}",

year = "2000",

month = jun,

day = "24",

doi = "10.1016/S0040-4039(00)00798-X",

language = "English",

volume = "41",

pages = "5141--5145",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "26",

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TY - JOUR

T1 - Regioselective asymmetric aminohydroxylation of precursors to 2,3,6- trideoxy-3-aminohexoses

AU - Davey, Roger M.

AU - Brimble, Margaret A.

AU - McLeod, Malcolm D.

PY - 2000/6/24

Y1 - 2000/6/24

N2 - The catalytic asymmetric aminohydroxylation (AA) of 5-substituted-pent- 2-enoates 8 and 17 was investigated as a route to 2,3,6-trideoxy-3- aminohexoses. The AA of ester 8, which bears a dimethyl acetal at C-5, favoured formation of the α-amino regioisomer 11 with optimum regioselectivity being observed using (DHQ)2AQN as the chiral ligand and the chloramine salt of ethyl carbamate as the nitrogen source. Ester 17, which has a 4-methoxyphenoxy group at C-5, undergoes highly regioselective AA affording the β-amino regioisomer 19 in excellent enantiomeric excess, thereby establishing that introduction of this aromatic group leads to a superior substrate for AA. (C) 2000 Elsevier Science Ltd.

AB - The catalytic asymmetric aminohydroxylation (AA) of 5-substituted-pent- 2-enoates 8 and 17 was investigated as a route to 2,3,6-trideoxy-3- aminohexoses. The AA of ester 8, which bears a dimethyl acetal at C-5, favoured formation of the α-amino regioisomer 11 with optimum regioselectivity being observed using (DHQ)2AQN as the chiral ligand and the chloramine salt of ethyl carbamate as the nitrogen source. Ester 17, which has a 4-methoxyphenoxy group at C-5, undergoes highly regioselective AA affording the β-amino regioisomer 19 in excellent enantiomeric excess, thereby establishing that introduction of this aromatic group leads to a superior substrate for AA. (C) 2000 Elsevier Science Ltd.

KW - Amino alcohols

KW - Asymmetric aminohydroxylation

KW - Asymmetric catalysis

KW - Asymmetric synthesis

KW - Osmium

UR - http://www.scopus.com/inward/record.url?scp=0034709563&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)00798-X

DO - 10.1016/S0040-4039(00)00798-X

M3 - Article

SN - 0040-4039

VL - 41

SP - 5141

EP - 5145

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Regioselective asymmetric aminohydroxylation of precursors to 2,3,6- trideoxy-3-aminohexoses

Abstract

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