. 2013 Oct 23;78(23):12243–12250. doi: 10.1021/jo4020485

Table 1. Optimization of Conditions for Metalation/Alkylation of SAMP Hydrazone (S)-1.

graphic file with name jo-2013-020485_0008.jpg

entry	base	additive	solvent	time (h)	product	conversion to 2 (%)/yield of 3 (%)
1	LDA		THF	2	2	59^a
2	ⁿBuLi		THF	1	2	90^a
3	^tBuLi		THF	1	2	90^a
4	ⁿBuLi		THF	1	3	45^b
5	ⁿBuLi	TMEDA	THF	1	3	45^b
6	ⁿBuLi		Et₂O	1	3	0^b
7	^tBuLi		THF	1	3	67^b
8	^tBuLi		THF	2	3	73^b

Determined by mass spectrometry.

Isolated yield after chromatography.