The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA

Iain Coldham; Daniele Leonori; Timothy K Beng; Robert E Gawley

doi:10.1039/B911024K

The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA

Iain Coldham, Daniele Leonori, Timothy K Beng, Robert E Gawley

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

Abstract

The kinetics of enantiomerization and dynamic thermodynamic resolution (DTR) of N-Boc-2-lithiopiperidine have been measured, revealing significant differences in enthalpy and entropy for these processes and a role for the achiral ligand TMEDA; the racemization and the DTR are catalytic and first order in [TMEDA], and this has implications for asymmetric synthesis with chiral organolithiums.

Original language	English
Pages (from-to)	5239-5241
Number of pages	2
Journal	Chemical Communications
DOIs	https://doi.org/10.1039/B911024K
Publication status	Published - 6 Aug 2009

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title = "The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA",

abstract = "The kinetics of enantiomerization and dynamic thermodynamic resolution (DTR) of N-Boc-2-lithiopiperidine have been measured, revealing significant differences in enthalpy and entropy for these processes and a role for the achiral ligand TMEDA; the racemization and the DTR are catalytic and first order in [TMEDA], and this has implications for asymmetric synthesis with chiral organolithiums.",

author = "Iain Coldham and Daniele Leonori and Beng, {Timothy K} and Gawley, {Robert E}",

year = "2009",

month = aug,

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doi = "10.1039/B911024K",

language = "English",

pages = "5239--5241",

journal = "Chemical Communications",

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T1 - The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA

AU - Coldham, Iain

AU - Leonori, Daniele

AU - Beng, Timothy K

AU - Gawley, Robert E

PY - 2009/8/6

Y1 - 2009/8/6

N2 - The kinetics of enantiomerization and dynamic thermodynamic resolution (DTR) of N-Boc-2-lithiopiperidine have been measured, revealing significant differences in enthalpy and entropy for these processes and a role for the achiral ligand TMEDA; the racemization and the DTR are catalytic and first order in [TMEDA], and this has implications for asymmetric synthesis with chiral organolithiums.

AB - The kinetics of enantiomerization and dynamic thermodynamic resolution (DTR) of N-Boc-2-lithiopiperidine have been measured, revealing significant differences in enthalpy and entropy for these processes and a role for the achiral ligand TMEDA; the racemization and the DTR are catalytic and first order in [TMEDA], and this has implications for asymmetric synthesis with chiral organolithiums.

U2 - 10.1039/B911024K

DO - 10.1039/B911024K

M3 - Article

SN - 1364-548X

SP - 5239

EP - 5241

JO - Chemical Communications

JF - Chemical Communications

ER -

The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA

Abstract

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