Bio-Based Chiral Amines via Aza-Michael Additions to (-)-Levoglucosenone Under Aqueous Conditions

Shi-Wei Kim; Edward T Ledingham; Shinji Kudo; Ben W Greatrex; Jonathan Sperry

doi:10.1002/ejoc.201800388

Bio-Based Chiral Amines via Aza-Michael Additions to (-)-Levoglucosenone Under Aqueous Conditions

Shi-Wei Kim, Edward T Ledingham, Shinji Kudo, Ben W Greatrex, Jonathan Sperry

Pharmacy

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15 Citations (Scopus)

Abstract

Chiral amines are highly coveted within the fine‐chemical industry and sustainable synthetic methodologies for their production are of great value. By harnessing the chirality present in cellulose‐derived (–)‐levoglucosenone (LGO), several bio‐based sp³‐rich amines containing up to four chiral centres have been readily prepared under aqueous conditions without using any catalysts, ligands, auxiliaries or resolutions.

Original language	English
Pages (from-to)	2028-2038
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	17
Early online date	8 Mar 2018
DOIs	https://doi.org/10.1002/ejoc.201800388
Publication status	Published - 8 May 2018

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title = "Bio-Based Chiral Amines via Aza-Michael Additions to (-)-Levoglucosenone Under Aqueous Conditions",

abstract = "Chiral amines are highly coveted within the fine‐chemical industry and sustainable synthetic methodologies for their production are of great value. By harnessing the chirality present in cellulose‐derived (–)‐levoglucosenone (LGO), several bio‐based sp³‐rich amines containing up to four chiral centres have been readily prepared under aqueous conditions without using any catalysts, ligands, auxiliaries or resolutions.",

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AU - Kim, Shi-Wei

AU - Ledingham, Edward T

AU - Kudo, Shinji

AU - Greatrex, Ben W

AU - Sperry, Jonathan

PY - 2018/5/8

Y1 - 2018/5/8

N2 - Chiral amines are highly coveted within the fine‐chemical industry and sustainable synthetic methodologies for their production are of great value. By harnessing the chirality present in cellulose‐derived (–)‐levoglucosenone (LGO), several bio‐based sp³‐rich amines containing up to four chiral centres have been readily prepared under aqueous conditions without using any catalysts, ligands, auxiliaries or resolutions.

AB - Chiral amines are highly coveted within the fine‐chemical industry and sustainable synthetic methodologies for their production are of great value. By harnessing the chirality present in cellulose‐derived (–)‐levoglucosenone (LGO), several bio‐based sp³‐rich amines containing up to four chiral centres have been readily prepared under aqueous conditions without using any catalysts, ligands, auxiliaries or resolutions.

UR - https://www.scopus.com/pages/publications/85046550753

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VL - 2018

SP - 2028

EP - 2038

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 17

ER -

Bio-Based Chiral Amines via Aza-Michael Additions to (-)-Levoglucosenone Under Aqueous Conditions

Abstract

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