Combining Q2MM Modeling and Kinetic Studies for Refinement of the Osmium-catalyzed Asymmetric Dihydroxylation (AD) Mnemonic

Peter Fristrup; Gitte Holm Jensen; Marie Louise Nygaard Andersen; David Ackland Tanner; Per-Ola Norrby

doi:10.1016/j.jorganchem.2005.11.009

Combining Q2MM Modeling and Kinetic Studies for Refinement of the Osmium-catalyzed Asymmetric Dihydroxylation (AD) Mnemonic

Peter Fristrup
, Gitte Holm Jensen
, Marie Louise Nygaard Andersen
, David Ackland Tanner
, Per-Ola Norrby

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

The interactions between the substrate and the ligand in the Sharpless AD reaction have been examined in detail, using a combination of substrate competition experiments and molecular modeling of transition states. There is a good agreement between computational and experimental results, in particular for the stereoselectivity of the reaction. The influence of each moiety in the second-generation ligand (DHQD)2PHAL on the rate and selectivity of the reaction has been elucidated in detail.

Original language	English
Journal	Journal of Organometallic Chemistry
Volume	691
Issue number	10
Pages (from-to)	2182-2198
ISSN	0022-328X
DOIs	https://doi.org/10.1016/j.jorganchem.2005.11.009
Publication status	Published - 2006

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title = "Combining Q2MM Modeling and Kinetic Studies for Refinement of the Osmium-catalyzed Asymmetric Dihydroxylation (AD) Mnemonic",

abstract = "The interactions between the substrate and the ligand in the Sharpless AD reaction have been examined in detail, using a combination of substrate competition experiments and molecular modeling of transition states. There is a good agreement between computational and experimental results, in particular for the stereoselectivity of the reaction. The influence of each moiety in the second-generation ligand (DHQD)2PHAL on the rate and selectivity of the reaction has been elucidated in detail.",

author = "Peter Fristrup and Jensen, \{Gitte Holm\} and Andersen, \{Marie Louise Nygaard\} and Tanner, \{David Ackland\} and Per-Ola Norrby",

year = "2006",

doi = "10.1016/j.jorganchem.2005.11.009",

language = "English",

volume = "691",

pages = "2182--2198",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

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T1 - Combining Q2MM Modeling and Kinetic Studies for Refinement of the Osmium-catalyzed Asymmetric Dihydroxylation (AD) Mnemonic

AU - Fristrup, Peter

AU - Jensen, Gitte Holm

AU - Andersen, Marie Louise Nygaard

AU - Tanner, David Ackland

AU - Norrby, Per-Ola

PY - 2006

Y1 - 2006

N2 - The interactions between the substrate and the ligand in the Sharpless AD reaction have been examined in detail, using a combination of substrate competition experiments and molecular modeling of transition states. There is a good agreement between computational and experimental results, in particular for the stereoselectivity of the reaction. The influence of each moiety in the second-generation ligand (DHQD)2PHAL on the rate and selectivity of the reaction has been elucidated in detail.

AB - The interactions between the substrate and the ligand in the Sharpless AD reaction have been examined in detail, using a combination of substrate competition experiments and molecular modeling of transition states. There is a good agreement between computational and experimental results, in particular for the stereoselectivity of the reaction. The influence of each moiety in the second-generation ligand (DHQD)2PHAL on the rate and selectivity of the reaction has been elucidated in detail.

U2 - 10.1016/j.jorganchem.2005.11.009

DO - 10.1016/j.jorganchem.2005.11.009

M3 - Journal article

SN - 0022-328X

VL - 691

SP - 2182

EP - 2198

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 10

ER -

Combining Q2MM Modeling and Kinetic Studies for Refinement of the Osmium-catalyzed Asymmetric Dihydroxylation (AD) Mnemonic

Abstract

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