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. 2018 Nov 20;140(49):17278–17289. doi: 10.1021/jacs.8b10816

Table 1. Dynamic Enantioselective Addition of Organozinc to Aromatic Aldehydes with (R)-1.

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a

General reaction conditions: 0.0125 mmol of (R,P,Sa/Ra)-1 in 0.5 mL of dry toluene at 0 °C; 0.375 mmol of R2Zn (Et2Zn, 1.0 M in hexane; i-Pr2Zn, 1.0 M in toluene) added dropwise and stirred over 10 min; 0.125 mmol of 11 added to the mixture. Reaction mixture stirred for 7 d at 0 °C. Reaction with irradiated mixture of (R)-1: 0.00125 mmol of (R,P,Sa/Ra)-1 in 15 mL of dry, degassed Et2O, irradiated with UV light (365 nm) for 30 min until the PSS was reached (S:MS = 17:83). PSS ratio determined by chiral HPLC analysis. Reaction procedure follows as described above.

b

Determined by 1H NMR analysis of crude.

c

Determined by chiral GC or chiral HPLC analysis of isolated product.

d

Isolated yield. Abbreviations: N.A., Not Applicable.