The asymmetric aminohydroxylation route to GABOB and homoserine derivatives

Michael Harding; Jennifer A. Bodkin; Fatiah Issa; Craig A. Hutton; Anthony C. Willis; Malcolm D. McLeod

doi:10.1016/j.tet.2008.11.037

The asymmetric aminohydroxylation route to GABOB and homoserine derivatives

Michael Harding, Jennifer A. Bodkin, Fatiah Issa, Craig A. Hutton, Anthony C. Willis, Malcolm D. McLeod^*

^*Corresponding author for this work

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

16 Citations (Scopus)

Abstract

The 4-nitrophenyl ether is an efficient directing group in the asymmetric aminohydroxylation reaction of homoallylic ether derivatives. Either regioisomeric product can be obtained with useful levels of enantioselectivity allowing for the short enantioselective synthesis of GABOB and homoserine derivatives. A model based on substrate-catalyst interactions is presented to explain the regio- and enantioselectivity of the aminohydroxylation reactions.

Original language	English
Pages (from-to)	831-843
Number of pages	13
Journal	Tetrahedron
Volume	65
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2008.11.037
Publication status	Published - 24 Jan 2009

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10.1016/j.tet.2008.11.037

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title = "The asymmetric aminohydroxylation route to GABOB and homoserine derivatives",

abstract = "The 4-nitrophenyl ether is an efficient directing group in the asymmetric aminohydroxylation reaction of homoallylic ether derivatives. Either regioisomeric product can be obtained with useful levels of enantioselectivity allowing for the short enantioselective synthesis of GABOB and homoserine derivatives. A model based on substrate-catalyst interactions is presented to explain the regio- and enantioselectivity of the aminohydroxylation reactions.",

keywords = "Amino acid, Asymmetric aminohydroxylation, Asymmetric catalysis, Osmium, Regioselective",

author = "Michael Harding and Bodkin, {Jennifer A.} and Fatiah Issa and Hutton, {Craig A.} and Willis, {Anthony C.} and McLeod, {Malcolm D.}",

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T1 - The asymmetric aminohydroxylation route to GABOB and homoserine derivatives

AU - Harding, Michael

AU - Bodkin, Jennifer A.

AU - Issa, Fatiah

AU - Hutton, Craig A.

AU - Willis, Anthony C.

AU - McLeod, Malcolm D.

PY - 2009/1/24

Y1 - 2009/1/24

N2 - The 4-nitrophenyl ether is an efficient directing group in the asymmetric aminohydroxylation reaction of homoallylic ether derivatives. Either regioisomeric product can be obtained with useful levels of enantioselectivity allowing for the short enantioselective synthesis of GABOB and homoserine derivatives. A model based on substrate-catalyst interactions is presented to explain the regio- and enantioselectivity of the aminohydroxylation reactions.

AB - The 4-nitrophenyl ether is an efficient directing group in the asymmetric aminohydroxylation reaction of homoallylic ether derivatives. Either regioisomeric product can be obtained with useful levels of enantioselectivity allowing for the short enantioselective synthesis of GABOB and homoserine derivatives. A model based on substrate-catalyst interactions is presented to explain the regio- and enantioselectivity of the aminohydroxylation reactions.

KW - Amino acid

KW - Asymmetric aminohydroxylation

KW - Asymmetric catalysis

KW - Osmium

KW - Regioselective

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U2 - 10.1016/j.tet.2008.11.037

DO - 10.1016/j.tet.2008.11.037

M3 - Article

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VL - 65

SP - 831

EP - 843

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

The asymmetric aminohydroxylation route to GABOB and homoserine derivatives

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