Table 1.

Substrate Scope^a,^b

Entry	Quinazolinone	Product	Yieldc	e.r.d
1			86%	97:3
2			79%	97:3
3			78%	96:4
4			79%	96:4
5			75%	93:7
6			63%	63:37
7			80%	65:35
8			85%	95:5
9			85%	93:7
10e			93%	96:4
11e			92%	99:1
12			89%	96:4
13			77%	98:2
14e			84%	56:44

^aReaction Conditions: quinazolinone 1 (0.10 mmol, 1 equiv), peptide 4q (0.01 mmol, 10 mol% w.r.t. 1), NBS (0.30 mmol, 3 equiv w.r.t. 1), PhMe/CHCl₃ (9:1 v/v) with 5% acetone additive (by volume), slow addition of NBS over 2.5 h.

^bData represent the average of two trials.

^cIsolated yields after chromatography are presented.

^dEnantiomer ratios were determined by chiral HPLC using OJ-H or AD-H columns.

^e2.0 equiv NBS was used in the bromination.