Diastereoselective sulfa-Michael reactions controlled by a biomass-derived chiral auxiliary

Julian Klepp; Harald Podversnik; Johannes Puschnig; Andrew Wallace; Ben W Greatrex

doi:10.1016/j.tet.2019.05.051

Diastereoselective sulfa-Michael reactions controlled by a biomass-derived chiral auxiliary

Julian Klepp
, Harald Podversnik
, Johannes Puschnig
, Andrew Wallace
, Ben W Greatrex

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

7 Citations (Scopus)

Abstract

A family of chiral auxiliaries derived from the lignocellulosic biomass pyrolysis product levoglucosenone (LGO) has been screened in the sulfa-Michael reaction. When promoted by inorganic bases with potassium counterions, the auxiliary with geminal benzyl substituents showed diastereoselectivity up to 90:10 for a broad range of α,β-unsaturated esters.

Original language	English
Pages (from-to)	3894-3903
Journal	Tetrahedron
Volume	75
Issue number	29
Early online date	28 May 2019
DOIs	https://doi.org/10.1016/j.tet.2019.05.051
Publication status	Published - 19 Jul 2019

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title = "Diastereoselective sulfa-Michael reactions controlled by a biomass-derived chiral auxiliary",

abstract = "A family of chiral auxiliaries derived from the lignocellulosic biomass pyrolysis product levoglucosenone (LGO) has been screened in the sulfa-Michael reaction. When promoted by inorganic bases with potassium counterions, the auxiliary with geminal benzyl substituents showed diastereoselectivity up to 90:10 for a broad range of α,β-unsaturated esters.",

author = "Julian Klepp and Harald Podversnik and Johannes Puschnig and Andrew Wallace and Greatrex, \{Ben W\}",

note = "Supplementary data to this article can be found online at https://doi.org/10.1016/j.tet.2019.05.051",

year = "2019",

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T1 - Diastereoselective sulfa-Michael reactions controlled by a biomass-derived chiral auxiliary

AU - Klepp, Julian

AU - Podversnik, Harald

AU - Puschnig, Johannes

AU - Wallace, Andrew

AU - Greatrex, Ben W

N1 - Supplementary data to this article can be found online at https://doi.org/10.1016/j.tet.2019.05.051

PY - 2019/7/19

Y1 - 2019/7/19

N2 - A family of chiral auxiliaries derived from the lignocellulosic biomass pyrolysis product levoglucosenone (LGO) has been screened in the sulfa-Michael reaction. When promoted by inorganic bases with potassium counterions, the auxiliary with geminal benzyl substituents showed diastereoselectivity up to 90:10 for a broad range of α,β-unsaturated esters.

AB - A family of chiral auxiliaries derived from the lignocellulosic biomass pyrolysis product levoglucosenone (LGO) has been screened in the sulfa-Michael reaction. When promoted by inorganic bases with potassium counterions, the auxiliary with geminal benzyl substituents showed diastereoselectivity up to 90:10 for a broad range of α,β-unsaturated esters.

U2 - 10.1016/j.tet.2019.05.051

DO - 10.1016/j.tet.2019.05.051

M3 - Article

SN - 0040-4020

VL - 75

SP - 3894

EP - 3903

JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

Diastereoselective sulfa-Michael reactions controlled by a biomass-derived chiral auxiliary

Abstract

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