Nature Communications

Table 1 Optimization of desymmetrization reaction^a

From: Desymmetrization of meso-bisphosphates using copper catalysis and alkylzirconocene nucleophiles


Entry	Cu salt	Ag salt^b	Ligand	Yield (%)	ee (%)
1	Cu1	–	A	71^c	0
2	CuClO₄	–	A	52^c	69
3	CuCl	AgOTf	A	64^c	66
4	CuCl	AgNTf₂	A	76^c	69
5	CuCl	AgNTf₂	B	61	65
6	CuCl	AgNTf₂	C	61	75
7	CuCl	AgNTf₂	D	67	83
8	CuCl	AgNTf₂	E	76	84
9	CuCl	AgNTf₂	F	70	86
10^d	CuCl	AgNTf₂	F	70	90
11^e	CuCl	AgNTf₂	F	27	92

^aReaction conditions: Alkene (2.5 eq.), Cp₂ZrHCl (2.0 eq.), CH₂Cl₂, then, Cu salt (10 mol%), Ligand (12 mol%), Ag Salt (15 mol%), CH₂Cl₂, then 1a (1.0 eq), 16 h. ee determined by HPLC. All products > 20:1 trans:cis
^bCatalyst solution filtered to remove AgCl
^cNMR yield
^d0 °C
^e–10 °C

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