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. Author manuscript; available in PMC: 2016 Dec 12.
Published in final edited form as: J Am Chem Soc. 2015 Jun 12;137(24):7632–7635. doi: 10.1021/jacs.5b04518

Table 3.

Hydrazone Hydrolysisa

graphic file with name nihms-834044-t0005.jpg
a

Conditions: 2 (0.06–0.08 mmol), paraformaldehyde (5–8 equiv), Amberlyst 15 (7–10 mg), acetone/H2O (10:1 or 1:1), r.t., 24–48 h (see SI for details) Ar′: 2-MeO-C6H4−

b

Isolated yield.

c

Determined by chiral phase HPLC; parentheses indicate ee of parent hydrazine; absolute stereochemistry was assigned by analogy to 2 (see SI).