Enantioselective synthesis of atropisomeric amides by dynamic resolution: Thermodynamic control with a proline-derived diamine resolving agent

Jonathan Clayden; Lai Wah Lai

doi:10.1002/(SICI)1521-3773(19990903)38:17<2556::AID-ANIE2556>3.0.CO;2-Q

Enantioselective synthesis of atropisomeric amides by dynamic resolution: Thermodynamic control with a proline-derived diamine resolving agent

Jonathan Clayden^*, Lai Wah Lai

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

95 Citations (Scopus)

Abstract

By exploiting the thermal instability about the Ar-CO axis at high temperature, atropisomeric amides can be dynamically resolved to provide material with up to 96.5% ee in 70-80% overall yield from racemic starting material. The amides are coupled with a diamine resolving agent and equilibrated to single diastereoisomers. Hydrolysis returns enantiomerically enriched amide (see reaction scheme).

Original language	English
Pages (from-to)	2556-2558
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	38
Issue number	17
DOIs	https://doi.org/10.1002/(SICI)1521-3773(19990903)38:17<2556::AID-ANIE2556>3.0.CO;2-Q
Publication status	Published - 3 Sept 1999

Research Groups and Themes

Organic & Biological

Keywords

Amides
Asymmetric synthesis
Atropisomerism
Dynamic resolution

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10.1002/(SICI)1521-3773(19990903)38:17<2556::AID-ANIE2556>3.0.CO;2-Q

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title = "Enantioselective synthesis of atropisomeric amides by dynamic resolution: Thermodynamic control with a proline-derived diamine resolving agent",

abstract = "By exploiting the thermal instability about the Ar-CO axis at high temperature, atropisomeric amides can be dynamically resolved to provide material with up to 96.5\% ee in 70-80\% overall yield from racemic starting material. The amides are coupled with a diamine resolving agent and equilibrated to single diastereoisomers. Hydrolysis returns enantiomerically enriched amide (see reaction scheme).",

keywords = "Amides, Asymmetric synthesis, Atropisomerism, Dynamic resolution",

author = "Jonathan Clayden and Lai, \{Lai Wah\}",

year = "1999",

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T1 - Enantioselective synthesis of atropisomeric amides by dynamic resolution

T2 - Thermodynamic control with a proline-derived diamine resolving agent

AU - Clayden, Jonathan

AU - Lai, Lai Wah

PY - 1999/9/3

Y1 - 1999/9/3

N2 - By exploiting the thermal instability about the Ar-CO axis at high temperature, atropisomeric amides can be dynamically resolved to provide material with up to 96.5% ee in 70-80% overall yield from racemic starting material. The amides are coupled with a diamine resolving agent and equilibrated to single diastereoisomers. Hydrolysis returns enantiomerically enriched amide (see reaction scheme).

AB - By exploiting the thermal instability about the Ar-CO axis at high temperature, atropisomeric amides can be dynamically resolved to provide material with up to 96.5% ee in 70-80% overall yield from racemic starting material. The amides are coupled with a diamine resolving agent and equilibrated to single diastereoisomers. Hydrolysis returns enantiomerically enriched amide (see reaction scheme).

KW - Amides

KW - Asymmetric synthesis

KW - Atropisomerism

KW - Dynamic resolution

UR - https://www.scopus.com/pages/publications/0033520371

U2 - 10.1002/(SICI)1521-3773(19990903)38:17<2556::AID-ANIE2556>3.0.CO;2-Q

DO - 10.1002/(SICI)1521-3773(19990903)38:17<2556::AID-ANIE2556>3.0.CO;2-Q

M3 - Article (Academic Journal)

AN - SCOPUS:0033520371

SN - 1433-7851

VL - 38

SP - 2556

EP - 2558

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 17

ER -

Enantioselective synthesis of atropisomeric amides by dynamic resolution: Thermodynamic control with a proline-derived diamine resolving agent

Abstract

Research Groups and Themes

Keywords

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