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.

Key words

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

References and Notes

• 1a Christoffers J. Eur. J. Org. Chem.  1998,  1259 
• 1b Krause N. Hoffmann-Röder A. Synlett  2001,  171 
• 1c Christoffers J. Synlett  2001,  723 
• 2a Narasaka K. Soai K. Mukaiyama T. Chem. Lett.  1974,  3:  1223 
• 2b Narasaka K. Soai K. Aikawa Y. Mukaiyama T. Bull. Soc. Chem. Jpn.  1976,  49:  779 
• 3 Kobayashi S. Suda S. Yamada M. Mukaiyama T. Chem. Lett.  1994,  23:  97 
• 4a Bernardi A. Karamfilova K. Boschin G. Scolastico C. Tetrahedron Lett.  1995,  36:  1363 
• 4b Bernardi A. Colombo G. Scolastico C. Tetrahedron Lett.  1996,  37:  8921 
• 5 Evans DA. Rovis T. Kozlowski MC. Tedrow JS. J. Am. Chem. Soc.  1999,  121:  1994 
• 6a Danishefsky S. Kitahara T. Schuda PF. Etheredge SJ. J. Am. Chem. Soc.  1976,  98:  3028 
• 6b Grieco PA. Ohfune Y. Majetich G. J. Org. Chem.  1979,  44:  3092 
• 6c Myers AG. McKinstry L. J. Org. Chem.  1996,  61:  2428 
• 6d Movassaghi M. Jacobsen EN. J. Am. Chem. Soc.  2002,  124:  2456 
• 7a Wheeler JW. Happ GM. Araujo J. Pasteels JM. Tetrahedron Lett.  1972,  46:  4635 
• 7b Rao YS. Chem. Rev.  1976,  78:  625 
• 7c Ravid U. Silverstein RM. Smith LR. Tetrahedron  1978,  34:  1449 
• 7d Bloch R. Gilbert L. J. Org. Chem.  1987,  52:  4603 
• 8a Nikishin GI. Svitanko IV. Troyansky EI. J. Chem. Soc., Perkin Trans. 2  1983,  595 
• 8b Ohkuma T. Kitamura M. Noyori R. Tetrahedron Lett.  1990,  31:  5509 
• 8c Tsuboi S. J. Org. Chem.  1998,  63:  1102 
• 8d Monetaña M. García F. Batalla C. Tetrahedron Lett.  2004,  45:  8549 
• 8e Teijeira M. Suárez PL. Gómez G. Terán C. Fall Y. Tetrahedron Lett.  2005,  46:  5889 
• 9a Casiraghi G. Rassu G. Synthesis  1995,  607 
• 9b Szlosek M. Franck X. Figadère B. Cavé A. J. Org. Chem.  1998,  63:  5169 
• 9c Evans DA. Kozlowski MC. Murry JA. Burgey CS. Campos KR. Connell BT. Staples RJ. J. Am. Chem. Soc.  1999,  121:  669 
• 9d Evans DA. Burgey CS. Kozlowski MC. Tregay SW. J. Am. Chem. Soc.  1999,  121:  686 
• 9e Casiraghi G. Zanardi F. Appendino G. Rassu G. Chem. Rev.  2000,  100:  1929 
• 10a Harding EK. Coleman MT. Liu LT. Tetrahedron Lett.  1991,  32:  3795 
• 10b Morimoto Y. Nishida K. Hayashi Y. Shirahama H. Tetrahedron Lett.  1993,  34:  5773 
• 10c Pelter A. Ward RS. Sirit A. Tetrahedron: Asymmetry  1994,  5:  1745 
• 10d Martin SF. Barr KJ. J. Am. Chem. Soc.  1996,  118:  3299 
• 11a Kitajima H. Katsuki T. Synlett  1997,  568 
• 11b Kitajima H. Ito K. Katsuki T. Tetrahedron  1997,  53:  17015 
• 11c Nishikori H. Ito K. Katsuki T. Tetrahedron: Asymmetry  1998,  9:  1165 
• 12 Desimoni G. Faita G. Filippone S. Mella M. Zampori MG. Zema M. Tetrahedron  2001,  57:  10203 
• 13 Suga H. Kitamura T. Kakehi A. Baba T. Chem. Commun.  2004,  1414 
• 14 Brown SP. Goodwin NC. MacMillan DWC. J. Am. Chem. Soc.  2003,  125:  1192 
• 15 Yang H. Hong Y.-T. Kim S. Org. Lett.  2007,  9:  2281 
• 16a Wada E. Yasuoka H. Kanemasa S. Chem. Lett.  1994,  23:  145 
• 16b Wada E. Yasuoka H. Kanemasa S. Chem. Lett.  1994,  23:  1637 
• 16c Wada E. Pei W. Kanemasa S. Chem. Lett.  1994,  23:  2345 
• 16d Wada E. Pei W. Yasuoka H. Chin U. Kanemasa S. Tetrahedron  1996,  52:  1205 
• 17a Zhao J.-L. Liu L. Sui Y. Liu Y.-L. Wang D. Chen Y.-J. Org. Lett.  2006,  8:  6127 
• 17b Landa A. Richter B. Johansen RL. Minkkilä A. Jørgensen KA. J. Org. Chem.  2007,  72:  240 
• 19a Utaka M. Watabu H. Takeda A. J. Org. Chem.  1987,  52:  4363 
• 19b Ronald RC. Ruder SM. Lillie TS. Tetrahedron Lett.  1987,  28:  131 
• 19c Yadav JS. Maniyan PP. Synth. Commun.  1993,  23:  2731 
• 19d Paddon-Jones GC. Moore CJ. Brecknell DJ. König WA. Kitching W. Tetrahedron Lett.  1997,  38:  3479 
• 19e Enholm EJ. Bhardawaj A. Tetrahedron Lett.  2003,  44:  3763 
• 19f Benincori T. Rizzo S. Pilati T. Ponti A. Sada M. Pagliarini E. Ratti S. Giuseppe C. Ferra L. Sannicolò F. Tetrahedron: Asymmetry  2004,  15:  2289 
• 20a Hunter CA. Sanders JKM. J. Am. Chem. Soc.  1990,  112:  5525 
• 20b Evans DA. Johnson JS. Olhava EJ. J. Am. Chem. Soc.  2000,  122:  1635 
• 20c Pandey MK. Bisai A. Singh VK. Tetrahedron Lett.  2006,  47:  897 
• 20d Zhao J.-L. Liu L. Sui Y. Liu Y.-L. Wang D. Chen Y.-J. Org. Lett.  2006,  8:  6127 

18

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).