Enantioselective Copper-Catalyzed O-H Insertion of α-Diazo Phosphonates

Abstract

A copper-catalyzed asymmetric O-H insertion of α-di­azo phosphonates with alcohols by using chiral spiro bisoxazoline ligands was developed. The insertion reaction exhibited good yields (up to 89%) with high enantioselectivities (up to 98% ee) and provided an efficient approach for synthesis of enantiomerically enriched α-alkoxy and hydroxy phosphonate derivatives starting from readily available materials.

Key words

asymmetric O-H insertion - chiral spiro ligands - copper catalysts - α-diazo phosphonates - α-alkoxy phosphonates

References and Notes

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8

NaBAr_F = sodium tetrakis[3,5-bis(trifluoromethyl)-phenyl]borate.

9

Box = 2,2′-(1-methylethyliene)bis(4,5-dihydro-4-tert-butyloxazole).

10

Pybox = 2,6-bis(4,5-dihydro-4-isopropyloxazole)pyridine.