Catalytic asymmetric propargyl- and allylboration of hydrazonoesters: a metal-free approach to sterically encumbered chiral α-amino acid derivatives

A new asymmetric catalytic propargyl- and allylboration of hydrazonoesters is reported. The reactions utilize allenyl- and allylboronic acids in the presence of the inexpensive parent BINOL catalyst. The reactions can be performed under mild conditions (0 °C) without any metal catalyst or other addi...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018-11, Vol.54 (91), p.12852-12855
Main Authors: Jonker, Sybrand J. T, Diner, Colin, Schulz, Göran, Iwamoto, Hiroaki, Eriksson, Lars, Szabó, Kálmán J
Format: Article
Language:English
Subjects:
Additives
Amino acids
Asymmetry
Catalysis
Catalysts
Crystallography
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Summary:A new asymmetric catalytic propargyl- and allylboration of hydrazonoesters is reported. The reactions utilize allenyl- and allylboronic acids in the presence of the inexpensive parent BINOL catalyst. The reactions can be performed under mild conditions (0 °C) without any metal catalyst or other additives affording sterically encumbered chiral α-amino acids. This is the first metal-free method for the asymmetric propargyl- and allylboration of hydrazonoesters. Metal-free asymmetric catalysis for the synthesis of sterically encumbered amino-acids was developed using allyl- and allenylboronic acid reagents.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/c8cc07908k