The enantioselective hydrophosphonylation of -Boc imines was investigated using a new family of pseudo-symmetric guanidine-thiourea catalysts, providing α-amino phosphonates in moderate to high yields with good enantioselectivity. The catalyst was heterogenized by polymerization with styrene and the resulting catalyst was applied to reactions under continuous-flow conditions.
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http://dx.doi.org/10.1039/d1ob01953h | DOI Listing |
J Am Chem Soc
December 2022
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AGGroningen, The Netherlands.
Controlling chiral recognition and chiral information transfer has major implications in areas ranging from drug design and asymmetric catalysis to supra- and macromolecular chemistry. Especially intriguing are phenomena associated with chiral self-recognition. The design of systems that show self-induced recognition of enantiomers, i.
View Article and Find Full Text PDFOrg Lett
November 2022
Department of Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
The first enantioselective hydrophosphonylation of ketimines with phosphine oxides was developed. The reaction of unprotected ketimines with phosphine oxides using a bis(imidazoline)-phosphoric acid catalyst gave chiral α-quaternary aminophosphorous compounds having a primary amino group in excellent yields and enantioselectivities. Based on experimental results and DFT calculation, transition states were proposed to explain the stereoselectivity of the reaction.
View Article and Find Full Text PDFOrg Biomol Chem
December 2021
Université Paris-Saclay, Institut de Chimie Moléculaire et des Matériaux d'Orsay, 91405 Orsay, France.
The enantioselective hydrophosphonylation of -Boc imines was investigated using a new family of pseudo-symmetric guanidine-thiourea catalysts, providing α-amino phosphonates in moderate to high yields with good enantioselectivity. The catalyst was heterogenized by polymerization with styrene and the resulting catalyst was applied to reactions under continuous-flow conditions.
View Article and Find Full Text PDFChemistry
August 2021
Key Laboratory of Green Chemistry & Technology of Ministry of Education College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, P. R. China.
ϵ-Benzosultam derivatives are potential drug candidates with diverse biological activities. A series of chiral ϵ-benzosultams bearing phosphorus functionalities was synthesized by catalytic asymmetric hydrophosphonylation in the presence of a bifunctional phosphonium salt catalyst. The desired hydrophosphonylation products were obtained in good yields with high enantioselectivities, and scale-up reactions and further derivations were successfully accomplished.
View Article and Find Full Text PDFOrg Lett
September 2018
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi , Hachioji , Tokyo 192-0392 , Japan.
The use of diaminomethylenemalononitrile (DMM) organocatalyst to promote the challenging 1,2-hydrophosphonylation of simple ketones and enones, which are also called α,β-unsaturated ketones, is proposed and validated. This reaction provided the corresponding chiral α-hydroxy phosphonates in high to excellent yields and with enantioselectivity up to 96% ee.
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