Table 1.

Optimization studies.

Entry	SiR3	7 a; X equiv	ROH	4 a; % Yield[a]
1	TMS (7 a)	1.2	–	19–45[b]
2	TMS (7 a)	1.2	MeOH	5
3	TMS (7 a)	1.2	iPrOH	34
4	TMS (7 a)	1.2	tBuOH	50
5	TMS (7 a)	2.0	tBuOH	25
6	TMS (7 a)	1.0	tBuOH	57
7	TMS (7 a)	0.7	tBuOH	64 (63)[c]
8	TES (7a′)	0.7	tBuOH	50[d]
9	TBS (7 a′′)	0.7	tBuOH	43[d]

Reactions performed with 0.46 mmol of 6. [a] ¹H NMR yield of 4 a. [b] Range of yields across 5 experiments, no detectable byproducts observed. [c] Yield of isolated 5 a (relative to limiting reagent 7) after silyl enol ether hydrolysis. [d] Yield of isolated 4 a relative to limiting reagent 7.