TY - JOUR
T1 - Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis
AU - Guasch, Joan
AU - Giménez-Nueno, Irene
AU - Funes-Ardoiz, Ignacio
AU - Bernús, Miguel
AU - Matheu, M. Isabel
AU - Maseras, Feliu
AU - Castillón, Sergio
AU - Díaz, Yolanda
PY - 2018/3/26
Y1 - 2018/3/26
N2 - © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Regio- and stereoselective oxyamination of dienes through a tandem rhodium-catalysed aziridination–nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine-based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.
AB - © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Regio- and stereoselective oxyamination of dienes through a tandem rhodium-catalysed aziridination–nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine-based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.
KW - enantioselectivity
KW - kinetic resolution
KW - organocatalysis
KW - oxyamination
KW - synthesis design
U2 - 10.1002/chem.201705670
DO - 10.1002/chem.201705670
M3 - Article
SN - 0947-6539
VL - 24
SP - 4635
EP - 4642
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 18
ER -