Table 2.

The substrate scope of the catalytic Mitsunobu reaction^[a]

Entry	Product		Catalytic yield [%][b]	Stoichiometric yield [%][b,c]
1		3 a	77	94
2		3 b	76	92
3		3 c	61	80
4		3 d	50	50
5		3 e	82	82
6		3 f	84	90
7		3 g	69[d]	77[d]
8		3 h	68[e]	78[e]
9		3 i	76	96
10		3 j	63	83
11		3 k	51[f]	85[f]
12		3 l	72	90
13		3 m	87[g,h]	98[g]
14		3 n	70[i]	93[i]

[a] Reactions performed on 0.5–1.0 mmol scale at 0.25 m employing 1.5 equiv of pronucleophile, 10 mol % loading of catalyst 2, and 1.1 equivalents of both DIAD and PhSiH₃. Reactions were all run at 80 °C. [b] Isolated average of two reactions. [c] Reactions performed at 23 °C with 1.5 equivalents of pronucleophile, TPP, and DIAD without phenylsilane for 18 h. [d] e.r. 94:6. [e] e.r.>99.5:0.5. [f] 48 h. [g] Concentration was 0.04 m. [h] Background reaction with only Boc-homoserine-OH, DIAD, and PhSiH₃ only produced traces. [i] N-Boc sulfamide (3 equiv) was used as the pronucleophile.