Synthesis, structures and catalytic activity of some BINOL based boronates and boronium salts

Shipra Garg, Daniel K. Unruh, Clemens Krempner

Research output: Contribution to journalArticlepeer-review

Abstract

The BINOL supported chiral boronate ester [C10H12O2BC6F5(THF)] [(R)-1], [C10H12O2BC6F5(O?PEt3)] [(R)-3] and [C10H12O2BC6F5]2[(R,R)-2] as well as the chiral boronium salts [C10H12O2B(O?PEt3)2]+[B(O2C10H12)2]-, [(R)-6] and [C10H12O2B(O?SMe2)2]+[B(O2C10H12)2]-[(R)-7] have been synthesized, characterized by NMR spectroscopy, and the solid state structures of [(R)-1], [(R,R)-2] and [(R)-3] determined. Chiral ester [(R)-1] was found to be a potent Lewis acid, similar to B(C6F5)3, and capable of rapidly catalyzing the annulation of (R)-, (S)- andrac-styrene oxide with nitrone PhCH?N(O)Me totrans-2-methyl-3,6-diphenyl-1,4,2-dioxazine (trans-11) with high regio- and diastereoslectivities.

Original languageEnglish
Pages (from-to)5044-5049
Number of pages6
JournalDalton Transactions
Volume50
Issue number14
DOIs
StatePublished - Apr 14 2021

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