Table 3:

Synthesis of hexahydro-6H-benzo[c]chromen-6-one diastereomers 7^[a]

Entry	R1	R2	7/Yield (%)[b]	dr[c] (7/6)	ee (%)[d]
1	Ph	H	7a/74	80:20	95
2	Ph	4-Cl	7b/67	79:21	90
3	Ph	4-Br	7c/70	78:22	90
4	Ph	4-Me	7d/65	77:23	98
5	Ph	4-MeO	7e/75	88:12	98
6	Ph	3-Me	7f/63	76:24	97
7	4-FC6H4	H	7g/62	79:21	96
8	4-ClC6H4	H	7h/67	77:23	95
9	4-MeC6H4H	H	7i/71	83:17	96
10	4-MeOC6H4	H	7j/72	84:16	98
11	Me	H	7k/49	82:18	84
12	t-Bu	H	7l/75	89:11	94
13[e]	Ph	H	7a/75	84:16	98

^[a]Unless otherwise indicated, all reactions were performed with 1 (0.14 mmol), 4 (0.12 mmol), and the modules 8d (0.012 mmol, 10 mol %) and 9d (0.012 mmol, 10 mol %) mmol) in toluene (0.5 mL) at rt for 16 h, followed by oxidation with PCC.

^[b]Yield of the major diastereomer isolated after column chromatography.

^[c]Ratio of 7/6, as determined by ¹H NMR analysis of the crude product.

^[d]Determined by HPLC analysis.

^[e]Reaction carried out at 1.0 mmol scale.