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. Author manuscript; available in PMC: 2011 Aug 22.
Published in final edited form as: Synthesis (Stuttg). 2008 Sep 1;2008(17):2669–2679. doi: 10.1055/s-2008-1067220

Table 1.

Reductive Aldol Cyclization of Aldo-Enones under Hydrogenation Conditions

graphic file with name nihms-317989-t0015.jpg
Substrate Catalyst Ligand Additive
(mol%)		 Yield of aldol
(syn/anti)		 Yield of
1,4-reduction
1a, n = 2, R = Ph Rh(PPh3)3Cl – – 2a, 1% (99:1) 95%
1a, n = 2, R = Ph Rh(cod)2OTf Ph3P – 2a, 21% (99:1) 25%
1a, n = 2, R = Ph Rh(cod)2OTf Ph3P KOAc (30) 2a, 59% (58:1) 21%
1a, n = 2, R = Ph Rh(cod)2OTf (4-F3CC6H4)3P – 2a, 57% (14:1) 22%
1a, n = 2, R = Ph Rh(cod)2OTf (4-F3CC6H4)3P KOAc (30) 2a, 89% (10:1) 0.1%
1b, n = 2, R = 4-MeOC6H4 Rh(cod)2OTf (4-F3CC6H4)3P KOAc (30) 2b, 74% (5:1) 3%
1c, n = 2, R = 2-naphthyl Rh(cod)2OTf (4-F3CC6H4)3P KOAc (30) 2c, 90% (10:1) 1%
1d, n = 2, R = 2-thienyl Rh(cod)2OTf (4-F3CC6H4)3P KOAc (30) 2d, 76% (19:1) 2%
1e, n = 2, R = 2-furyl Rh(cod)2OTf (4-F3CC6H4)3P KOAc (30) 2e, 70% (6:1) 10%
1f, n = 1, R = Ph Rh(cod)2OTf (4-F3CC6H4)3P KOAc (30) 2f, 71% (24:1) 1%
1g, n = 2, R = Me Rh(cod)2OTf (4-F3CC6H4)3P KOAc (30) 2g, 65% (1:5) –