Enantioselective hydrophosphonylation of N -Boc imines using chiral guanidine-thiourea catalysts

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...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-12, Vol.19 (48), p.10560-10564
Main Authors: Chassillan, Louis, Yamashita, Yasuhiro, Yoo, Woo-Jin, Toffano, Martial, Guillot, Régis, Kobayashi, Shū, Vo-Thanh, Giang
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Chemical Sciences
Continuous flow
Enantiomers
Guanidine
Imines
Organic chemistry
Phosphonates
Styrene
Thiourea
Thioureas
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01953h