Catalytic Enantioselective Mukaiyama-Michael Reaction of 2-(Trimethyl­silyloxy)furan with α′-Phenylsulfonyl Enones

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.

asymmetric catalysis - Michael additions - Lewis acids - ligands - lactones

References and Notes

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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).

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