Nature Communications

Table 1 Reaction condition optimization

From: Chiral aldehyde-nickel dual catalysis enables asymmetric α−propargylation of amino acids and stereodivergent synthesis of NP25302


Entry	3	Ligand	LG	Yield (%)^a	ee (%)^b
1	3a	L1	OBz	46	95
2	3a	L1	OAc	49	94
3	3a	L1	OBoc	34	90
4	3a	L1	OCO₂Me	18	74
5	3a	L1	OPO(OEt)₂	14	76
6^c	3a	L1	OAc	71	93
7^c	3a	L2	OAc	6	22
8^c	3a	L3	OAc	10	87
9^c	3a	L4	OAc	80	91
10^c	3b	L4	OAc	64	97
11^c	3c	L4	OAc	11	94
12^c	3d	L4	OAc	70	94
13^c	3e	L4	OAc	78	90
14^c	3 f	L4	OAc	63	93
15^c	3 g	L4	OAc	14	94
16^c	3 h	L4	OAc	83	96
17^c	3i	L4	OAc	87	96
18^c	3j	L4	OAc	9	40
19^c	3k	L4	OAc	0	–
20^c	3 l	L4	OAc	33	82
21^c	3 m	L4	OAc	0	–
22 ^cd	3i	L4	OAc	92	96
23 ^cd	ent-3i^e	L4	OAc	25	62
24^cdf	3a	L1	OAc	trace	–

^aIsolated yield.
^bDetermined by chiral HPLC.
^cWith 160 mol% TMG.
^dWith 0.5 mL PhCH₃.
^eent-3i = the enantiomer of chiral aldehyde 3i.
^fNi(COD)₂ was replaced by Pd(PPh₃)₄ or [Pd(C₃H₅)Cl]_2.

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