Enantioselective synthesis of: Anti -3-alkenyl-2-amido-3-hydroxy esters: Application to the total synthesis of (+)-alexine

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TY - JOUR

T1 - Enantioselective synthesis of

T2 - RSC Advances

AU - Yu, Lu

AU - Somfai, Peter

PY - 2019

Y1 - 2019

N2 - A straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic α-amino-β-keto esters by using a ATH/DKR protocol has been developed. This method gives moderate to excellent yields with high chemo-, diastereo- and enantioselectivities for a broad range of substrates. In order to highlight the versatility of the methodology it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.

AB - A straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic α-amino-β-keto esters by using a ATH/DKR protocol has been developed. This method gives moderate to excellent yields with high chemo-, diastereo- and enantioselectivities for a broad range of substrates. In order to highlight the versatility of the methodology it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.

U2 - 10.1039/c9ra00173e

DO - 10.1039/c9ra00173e

M3 - Article

VL - 9

SP - 2799

EP - 2802

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

IS - 5

ER -