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DOI: 10.1055/s-2008-1032074
Catalytic Enantioselective Mukaiyama-Michael Reaction of 2-(Trimethylsilyloxy)furan with α′-Phenylsulfonyl Enones
Publication History
Publication Date:
23 January 2008 (online)
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Abstract
The Mukaiyama-Michael reaction of 2-(trimethylsilyloxy)furan with α′-phenylsulfonyl enones using bis(oxazoline)-copper(II) complexes as chiral catalyst provides the γ-butenolides in high enantio- and diastereoselectivity. This approach is very useful for the enantioselective synthesis of γ-butenolide derivatives under chiral Lewis acid catalysis.
Key words
asymmetric catalysis - Michael additions - Lewis acids - ligands - lactones
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References and Notes
Typical Procedure for the Mukaiyama-Michael Reaction of 2-(Trimethylsilyloxy)furan (3) with α′-Phenylsulfonyl Enone 5a: To the flask of freshly prepared [(4R,5S)-diPhBox]Cu(OTf)2 (5 mol%) in CHCl3 (1 mL) was added a solution of α′-phenylsulfonyl enone 5a (0.11 mmol, 25 mg) in CHCl3 (1 mL). After being stirred at r.t. for 0.5 h, the reaction mixture was cooled to 0 °C, and the solution of 3 (0.22 mmol, 35 mg) in CHCl3 (1 mL) was added to the reaction mixture. The reaction was maintained at the desired temperature until a complete consumption of the α′-phenylsulfonyl enone 5a as monitored by TLC. After completion of the reaction, the reaction was quenched with sat. aq NaHCO3 solution, extracted with CH2Cl2, washed with H2O, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 6a as an oil in 99% yield (34 mg). Spectroscopic data for 6a: 1H NMR (400 MHz, CDCl3): δ = 1.01 (d, J = 6.9 Hz, 3 H), 2.41 (m, 1 H), 2.60 (dd, J = 18.8, 7.2 Hz, 1 H), 2.84 (dd, J = 18.8, 5.3 Hz, 1 H), 4.14 (dd, J = 21.4, 13.3 Hz, 2 H), 4.90 (dd, J = 6.1, 3.2 Hz, 1 H), 6.08 (dd, J = 5.8, 1.9 Hz, 1 H), 7.43 (d, J = 5.9 Hz, 1 H), 7.56 (t, J = 8.0 Hz, 2 H), 7.67 (t, J = 7.7 Hz, 1 H), 7.84 (d, J = 7.4 Hz, 2 H). 13C NMR (100 MHz, CDCl3): δ = 16.02, 31.88, 46.12, 66.86, 85.73, 122.26, 128.05, 129.34, 134.32, 138.60, 154.66, 172.39, 196.34. IR (KBr): 3700, 3139, 3022, 2953, 2360, 1731, 1612, 1566, 1490, 1432, 1353, 1223, 1116, 1060, 1005, 946, 870, 783, 720, 669 cm-1. HRMS (ESI): m/z [M + H]+ calcd for C15H17O5S: 309.0798; found: 309.0791. Product ratio was determined by HPLC analysis (Chiralcel OD-H, 30%
i-PrOH-hexane, 0.6 mL/min, λ = 254 nm); S,S-isomer (major): t
R = 42.4 min and R,R-isomer (minor): t
R = 53.7 min; [α]D
25 +58.7° (c = 1.0 in CH2Cl2).