Table 2.

Catalytic Enantioselective Synthesis of 3-Acyloxy-1-alkenes^a

Entrya	R1	R2	3	time [h]	4	yield [%]b	ee [%]c (config)
1	n-Pr	Me	3b	17	4b	88	94 (R)d
2e	n-Pr	Ph	3b	16	4b	98	94 (R)f
3	i-Bu	Me	3c	14	4d	96	93
4	Cy	Me	3d	48	4h	45	90
5	(CH2)2Ph	Ph	3e	17	4i	85	93g
6	CH2OH	Me	3f	17	4e	92	97 (S)h
7	CH2OAc	Me	3g	8	4a	90	99 (S)h
8	CH2OPMB	Me	3h	16	4f	93	99 (S)h
9	(CH2)3OTBS	Me	3i	17	4g	98	93 (R)i
10j	(CH2)3OTBS	Ph	3i	20	4j	93	99(S)d,g

^a[(R_p,S)-COP-OAc]₂ (2) except for entry 10 that used ent-2.

^bYield of pure product.

^cDetermined by GC analysis unless otherwise indicated; results of duplicate experiments agreed within ±2%.

^dAbsolute configuration determined by analysis of the Mosher ester.³⁴

^e[3] = 0.17 M.

^fAbsolute configuration by optical rotation.³⁵

^gDetermined by HPLC analysis.

^hAbsolute configuration by synthesis from (S)-3-butene-1,2-diol.

ⁱAbsolute configuration by optical rotation.³⁶

^jCatalyst was ent-2.