Updating the asymmetric osmium-catalyzed dihydroxylation (AD) mnemonic. Q2MM modeling and new kinetic measurements

Peter Fristrup; David Ackland Tanner; Per-Ola Norrby

doi:10.1002/chir.10214

Updating the asymmetric osmium-catalyzed dihydroxylation (AD) mnemonic. Q2MM modeling and new kinetic measurements

Peter Fristrup, David Ackland Tanner, Per-Ola Norrby

Department of Chemistry

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

Abstract

The mnemonic device for predicting stereoselectivities in the Sharpless asymmetric dihydroxylation (AD) reaction has been updated based on extensive computational studies. Kinetic measurements from competition reactions validate the new proposal. The interactions responsible for the high stereoselectivity in the title reaction are analyzed in detail and mapped onto the mnemonic device.

Original language	English
Journal	Chirality
Volume	15
Issue number	4
Pages (from-to)	360-368
ISSN	0899-0042
DOIs	https://doi.org/10.1002/chir.10214
Publication status	Published - 2003

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title = "Updating the asymmetric osmium-catalyzed dihydroxylation (AD) mnemonic. Q2MM modeling and new kinetic measurements",

abstract = "The mnemonic device for predicting stereoselectivities in the Sharpless asymmetric dihydroxylation (AD) reaction has been updated based on extensive computational studies. Kinetic measurements from competition reactions validate the new proposal. The interactions responsible for the high stereoselectivity in the title reaction are analyzed in detail and mapped onto the mnemonic device.",

author = "Peter Fristrup and Tanner, {David Ackland} and Per-Ola Norrby",

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AU - Fristrup, Peter

AU - Tanner, David Ackland

AU - Norrby, Per-Ola

PY - 2003

Y1 - 2003

N2 - The mnemonic device for predicting stereoselectivities in the Sharpless asymmetric dihydroxylation (AD) reaction has been updated based on extensive computational studies. Kinetic measurements from competition reactions validate the new proposal. The interactions responsible for the high stereoselectivity in the title reaction are analyzed in detail and mapped onto the mnemonic device.

AB - The mnemonic device for predicting stereoselectivities in the Sharpless asymmetric dihydroxylation (AD) reaction has been updated based on extensive computational studies. Kinetic measurements from competition reactions validate the new proposal. The interactions responsible for the high stereoselectivity in the title reaction are analyzed in detail and mapped onto the mnemonic device.

U2 - 10.1002/chir.10214

DO - 10.1002/chir.10214

M3 - Journal article

SN - 0899-0042

VL - 15

SP - 360

EP - 368

JO - Chirality

JF - Chirality

IS - 4

ER -

Updating the asymmetric osmium-catalyzed dihydroxylation (AD) mnemonic. Q2MM modeling and new kinetic measurements

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