Table 2.

Asymmetric cycloisomerization reactions.^a

Entry	Substrate	Product	Yield[%]	ee [%]
1	1	1a	86	>99b
2	2	2a	90	97b
3	3	3a	45	29c
4	4	4a	85	>98c
5	5	5a	75	98c
6d	6	6a	89	93b
7	7:E=CooMe	7a	78	97c
8d	8:E=Cooipr	8a	84	>98c
9d	9:E=So2ph	9a	92	87c
10	10	10a	85	>98c
11	11	11a	92	>99b
12d	12	12a	93	>98e
13d	13	13a	83	94f

^aReactions were run in DCE (0.4 M) in the presence of 10 mol % [Rh((S)-BINAP)]SbF₆ at 23 °C for 12–16 h.

^bMeasured by chiral HPLC (OD-H column) after derivatization to the corresponding p-bromobenzoate ester or ethylene glycol acetal.

^cMeasured by ¹H and ¹⁹F NMR spectroscopic analysis of the corresponding Mosher ester.

^dReactions were run in acetone as solvent.

^eMeasured by ¹H NMR spectroscopic analysis of the corresponding Mosher ester prepared through sequential dihydroxylation-cleavage, reduction, and esterification.

^fMeasured by chiral HPLC (OD-H column) after sequential acid hydrolysis, reduction, and derivatization to the corresponding p-bromobenzoate ester.