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. Author manuscript; available in PMC: 2011 Nov 15.
Published in final edited form as: Angew Chem Int Ed Engl. 2010 Nov 15;49(47):8930–8933. doi: 10.1002/anie.201003470

Table 2.

Substrate scope for deprotection/diastereoselective Henry cyclization cascade.

graphic file with name nihms257796t2.jpg
Product[a] R t [h] Yield [%] d.r.
9a Ph 3 78 >20:1
9b 4-Cl-C6H5 7 69 20:1
9c 2-thienyl 3 94 20:1
9d 2-furyl 3 54 20:1
9e (E)-CH=CH-C6H4 12 64 3:1
9 f H 12 70 1.5:1
9g n-pentyl 12 58 5:1
9h iPr 16 56 >20:1
9i tBu 16 59 >20:1
[a]

Reagents: Silyl enol ether 8a–i (1 equiv), NaOH (1.2 equiv), [8]0= 0.01m in (1:1) MeOH:CH2Cl2.

[b]

Stereostructures were determined through NOESY experiments and X-ray crystallography.