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. Author manuscript; available in PMC: 2017 Mar 1.
Published in final edited form as: Angew Chem Int Ed Engl. 2016 Feb 4;55(10):3455–3458. doi: 10.1002/anie.201600309

Chart 1.

Chart 1

Scope of the method. [a] Conv. refers to the consumption of allylic phosphate and was determined by analysis of 1H NMR spectra of unpurified reaction mixtures (the same for SN2′:SN2 ratios); ≤5% linear methoxy addition products are observed in all cases. For 12h-k the mixture was treated with NaIO4/NH4OAc at 22 °C for 1 h (1/1 acetone/H2O). [b] Yield refers to isolated and pure SN2′ isomers, except for 12k (5% linear product isomer), 12l (3% boryl addition byproduct) and 12n (3% product from Z isomer of the substrate). Enantioselectivities were determined by HPLC analysis. See the Supporting Information for details.