Table 1.

Synthesis of α-amino esters 1b–al via α-hydroxyimino esters 2a–al.

Ar	R	% 2a	% 1
a	Ph	60	nd
b	2-MeC6H4	61	85
c	3-MeC6H4	63	85
d	4-MeC6H4	60	87
e	4-iPrC6H4	48	91
f	cyclopentyl	35	85
g	cyclohexyl	50	92
h	2-CF3C6H4	39	86
i	3-CF3C6H4	41	78
j	4-CF3C6H4	62	91
k	2-FC6H4	57	88
l	3-FC6H4	65	89
m	4-FC6H4	–	81b
n	2,4-F2C6H3	50	85
o	2,6-F2C6H3	54	94
p	2,3-F2C6H3	51	92
q	2,5-F2C6H3	50	95
r	3,5-F2C6H3	46	84
s	2,3,5-F3C6H2	35	94
t	2-ClC6H4	23/49c	94
u	3-ClC6H4	26/59c	92
v	4-ClC6H4	37/62c	85
w	4-BrC6H4	42	86
x	2-MeOC6H4	60	83
y	3-MeOC6H4	–	75b
z	2-BnOC6H4	48	91
aa	3-BnOC6H4	37	92
ab	4-BnOC6H4	40	94
ac	2-pyridyl	49	56
ad	3-pyridyl	43	63
ae	furan-2-yl	33/47d	89
af	5-methylfuran-2-yl	33	88
ag	4,5-dimethylfuran-2-yl	10/23e	90
ah	5-ethylfuran-2-yl	34	94
ai	5-trifluoromethylfuran-2-yl	36	95
aj	5-ethylthiophen-2-yl	29	92
ak	3-methylthiophen-2-yl	32	89
al	4,5-dimethylthiophen-2-yl	31	87

^aIsolated yield from aldehydes 5. ^bOverall isolated yield from aldehydes 5m or 5y. ^cReactions run in isopropanol and NMe₄BH₄ used as a reductant. ^dReduction run at –10 °C for 90 minutes. ^eSame as note d but using a THF/ethanol mixture.