Table 2.

Scope of the Tandem Two-Component Etherification Reactions (eq 1; 1, R = Et; R¹ = Bn)^a

entry	1; R2=	R3Si-Nub	cyclic ether 2/3Nu=		ds = 2:3c	yield (%)f
1	H	A	-CH2CH=CH2	a	≥99:1d	90
2	Me	A	“	b	≥19:1	88
3	H	B	-CH=C=CH2	c	≥19:1e	80
4	Me	B	“	d	≥19:1e	72
5	H	C	-CH2C(O)CH3	e	≥19:1	73
6	Me	C	“	f	≥19:1	80
7	2H	D	-H	g	≥19:1	85
8	Me	D	“	h	≥99:1d	95

^aAll reactions were carried out on a 0.2-0.3 mmol reaction scale in CH₃CN at room temperature using 5-10 mol % BiBr₃ and 1.2-3.0 equiv. of R₃Si-Nu.

^bA = Me₃SiCH₂CH=CH₂; B = Me₃SiCH₂C≡CH; C = CH₂=C(OSiMe₃)CH₃; D = Et₃SiH.

^cRatios of diastereoisomers were determined by 400 MHz ¹H NMR on the crude reaction mixture unless otherwise indicated.

^dDetermined by capillary GLC.

^eContaminated with 5-10% of the propargylated derivative.

^fIsolated yields.