Table 2.

Scope for the Synthesis of Racemic α-Aryl α-Amino Esters 8a–l^a

Entry	N factorb	Method A — Step 3 — Method B		Product
		(Time, Temp, yield)	(Time, Temp, yield)
1	−1.18	10 d, RT, <10%	24 h, 60 °C, 48%e (6:1 rr)c,d
2	1.36	14 d, RT, <10%	17 h, RT, 59%c,e
3	ND	2 d, 60 °C, 34% (2:1 rr)d	16 h, RT, 72%e
4	2.00	1.5 d, 60 °C, 74%	18 h, 60 °C, 82%e
5	ND	48 h, 40 °C, 10%	96 h, 0 °C, 41%e
6	2.48	9 h, 60 °C, 82%e (5:1 rr)d 36 h, 60 °C, 61% (10:1 rr)d	2 h, RT, 74% (5:1 rr)d —
7	ND	1.5 d, 60 °C, 71%e (>20:1 rr)d	4 h, 60 °C, 74% (2:1 rr)d
8	4.63	0.5 h, −60 °C, 67%e	10 min, −40 °C, 45%
9f	5.50	24 h, 40 °C, 46%e	12 h, RT, 66%
10	5.55	2 h, 0 °C, 64%e	15 min, −40 °C, 42%
11	5.75	3 h, −45 °C, 79%e	30 min, −40 °C, 56%
12	5.85	1.5 h, 0 °C, 62%e	15 h, −40 °C, 58%

^aMethod A: reaction performed in CHCl₃, steps 1/2 for 12 h. Method B: reaction performed in CH₃CN, steps 1/2 for 24 h. Both methods are followed by the addition of arenes (step 3) for the specified time and temperature. Isolated yields are reported.

^bFactors of nucleophilicity have been previously reported in CH₃CN or CH₂Cl₂.

^cAn excess of arenes (3.0 equiv) was used, and the isolated yields for 8a and 8b are 60% and 71%, respectively.

^dRatio of regioisomers (para/ortho) are reported (rr) based on ¹H NMR integration values.

^eSynthesis of these compounds was previously reported. See ref 18.

^fThe employed nucleophile is aniline hydrochloric salt.