Table 3.

Lithiation-substitution of enantioenriched N-Boc-2-aryl pyrrolidines using indicated conditions, except as noted.

Entry	Ar	er (R:S)	E+	Product	% Yield	er
1	Ph	96:4	Me2SO4	R-25	86a	94:6
2	Ph	96:4	DMF	R-26	83b (88c)	>99:1
3	Ph	96:4	EtOCOCl	R-27	70b (79c)	94:6
4	Ph	96:4	(CD3)2CO	R-28	85b (92c)	94:6
5	Ph	96:4	2-bromotoluene	R-29	8b,d	92:8
6	Ph	50:50	2-bromotoluene	rac-29	12a,d,e	50:50
7	2-tolyl	90:10	MeOD	R-19·d1	100c	90:10
8	2-pyridyl	90:10	MeOD	R-20·d1	100c	90:10
9	1-Np	95:5	MeOD	R-21·d1	100c	95:5
10	1-Np	95:5	Me2SO4	R-31	91a	95:5
11	1-Np	95:5	PhBr	S-32	<5c,d,e	95:5
12	4-(NC)-C6H4	7:93	MeOD	S-22·d1	100c	93:7

^aisolated yield,

^bisolated yield of C2 and C5 substitution products after deprotonation by s-BuLi/TMEDA,

^cpercent conversion by GC after deprotonation using n-BuLi/TMEDA,

^dvia Pd-catalyzed coupling for 48 h at 40 °C,

^elithiated in the absence of TMEDA.