Optimization of reaction conditions for intramolecular hydroamination of 1c^a.

Entrya	Variation from standard conditions	Yieldb
1	(None)	97% (92%)
2	AcOH in place of 1-AdaCO2H	89%
3	PivOH in place of 1-AdaCO2H	92%
4	PhCO2H in place of 1-AdaCO2H	87%
5	A1 in place of 1-AdaCO2H	90%
6	A2 in place of 1-AdaCO2H	88%
7	PhMe as solvent	82%
8	PhCN as solvent	88%
9	t-AmylOH as solvent	77%
10	TFE as solvent	77%
11	HFIP as solvent	65%
12c	80 °C	91%
13	120 °C	78%
14	0.5 M	96%
15	2.0 M	90%
16d	DG1 in place of AQ	44%
17d	DG2 in place of AQ	16%
18d	OH in place of AQ	n.d.

^a1c (0.1 mmol).

^{b 1}H NMR yield with CH₂Br₂ as internal standard; isolated yield given in parentheses.

^c40 h.

^d1c (0.05 mmol).