Samarium Diiodide Promoted Tandem β-Elimination and Cross-Pinacol Coupling: A New Access to 1-Vinyl-1,2-diols with Two Adjacent Quaternary Carbon Centers

Abstract

A samarium diiodide promoted tandem β-elimination/cross-pinacol coupling was developed. A series of novel 1-vinyl-1,2-diols with two adjacent quaternary carbon centers were obtained in moderate to good yields. Possible reaction pathways are proposed.

Key words

samarium diiodide - cross-pinacol coupling - 1,2-diol - quaternary carbon center - tandem reaction

• References


For reviews, see:
• 1a Casiraghi G, Zanardi F, Rassu G, Spanu P. Chem. Rev. 1995; 95: 1677
• 1b Fu GC In Modern Carbonyl Chemistry . Otera J. Wiley-VCH; Weinheim: 2000: 69-91
• 1c Dushin RG In Comprehensive Organometallic Chemistry II . Vol. 12. Hegedus LS. Pergamon; Oxford: 1995: 1071-1095
• 1d Robertson M In Comprehensive Organic Synthesis I . Vol. 3. Trost BM. Pergamon; New York: 1991: 563-611

For selected examples, see:
• 1e Hinakubo Y, Matsukawa S. Org. Lett. 2003; 5: 1221
• 1f Li TH, Chan TH. Org. Lett. 2000; 2: 1129
• 1g Wang CY, Pan YJ, Wu AX. Tetrahedron 2007; 63: 429
• 1h Buchammagari H, Toda Y, Hirano M, Hosono H, Takeuchi D, Osakada K. Org. Lett. 2007; 9: 4287
• 1i Takenaka N, Xia GY, Yamamoto H. J. Am. Chem. Soc. 2004; 126: 13198
• 1j Hirao T, Xu XL. J. Org. Chem. 2005; 70: 8594
• 1k Yang HW, Wang HS, Zhu CJ. J. Org. Chem. 2007; 72: 10029
• 1l Ueda T, Kanomata N, Machida H. Org. Lett. 2005; 7: 2365
• 1m Aspinall HC, Greeves N, Valla C. Org. Lett. 2005; 7: 1919
• 1n Handy ST, Omune D. Org. Lett. 2005; 7: 1553
• 1o Groth U, Jeske M. Angew. Chem. Int. Ed. 2000; 39: 574

For selected examples, see:
• 2a Hashmi AS. K, Bührle M, Wölfle M, Rudolph M, Wieteck M, Rominger F, Frey W. Chem.–Eur. J. 2010; 16: 9846
• 2b Trost BM, Amans D, Seganish WM, Chung CK. J. Am. Chem. Soc. 2009; 131: 17087
• 3a Trost BM, Jiang CH. Synthesis 2006; 369
• 3b Christoffers J, Baro A. Adv. Synth. Catal. 2005; 347: 1473
• 3c Douglas CJ, Overman LE. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5363
• 3d Denissova I, Barriault L. Tetrahedron 2003; 59: 10105
• 3e Christoffers J, Mann A. Angew. Chem. Int. Ed. 2001; 40: 4591
• 4a Chiara JL, Cabri W, Hanessian S. Tetrahedron Lett. 1991; 32: 1125
• 4b Molander GA, Kenny C. J. Org. Chem. 1988; 53: 2132
• 4c Kim SM, Byun IS, Kim YH. Angew. Chem. Int. Ed. 2000; 39: 728
• 4d Kleiner G, Tarnopolsky A, Hoz S. Org. Lett. 2005; 7: 4197
• 5a Konradi AW, Kemp SJ, Pedersen SF. J. Am. Chem. Soc. 1994; 116: 1316
• 5b Kraynack EA, Pedersen SF. J. Org. Chem. 1993; 58: 6114
• 5c Groth U, Jung M, Vogel T. Chem.–Eur. J. 2005; 11: 3127
• 5d Takai K, Morita R, Toratsu C. Angew. Chem. Int. Ed. 2001; 40: 1116
• 5e Takai K, Morita R, Matsushita H, Toratsu C. Chirality 2003; 15: 17
• 5f Yang YS, Shen ZL, Loh TP. Org. Lett. 2010; 12: 3788

For selected examples, see:
• 6a Seebach D, Oei HA. Angew. Chem., Int. Ed. Engl. 1975; 14: 634
• 6b Horner L, Klaus J. Liebigs Ann. Chem. 1979; 1232
• 6c Muroi M, Inouye Y, Ohno M. Bull. Chem. Soc. Jpn. 1969; 42: 2948
• 6d Kim SM, Byun IS, Kim YH. Angew. Chem. Int. Ed. 2000; 39: 728
• 7a Xu M.-H, Wang W, Lin G.-Q. Org. Lett. 2000; 2: 2229
• 7b Wang W, Xu M.-H, Lei X.-S, Lin G.-Q. Org. Lett. 2000; 2: 3773
• 7c Xu M.-H, Wang W, Xia L.-J, Lin G.-Q. J. Org. Chem. 2001; 66: 3953
• 7d Wang W, Zhong Y.-W, Lin G.-Q. Tetrahedron Lett. 2003; 44: 4613
• 7e Zhong Y.-W, Izumi K, Xu M.-H, Lin G.-Q. Org. Lett. 2004; 6: 4747
• 7f Zhong Y.-W, Xu M.-H, Lin G.-Q. Org. Lett. 2004; 6: 3953
• 7g Huang L.-L, Xu M.-H, Lin G.-Q. J. Org. Chem. 2005; 70: 529
• 7h Zhong Y.-W, Dong Y.-Z, Fang K, Xu M.-H, Lin G.-Q. J. Am. Chem. Soc. 2005; 127: 11956
• 7i Zhu C, Shi Y, Xu M.-H, Lin G.-Q. Org. Lett. 2008; 10: 1243
• 7j Sun X.-W, Wang W, Xu M.-H, Lin G.-Q. Tetrahedron Lett. 2008; 49: 5807
• 7k Sun X.-W, Xu M.-H, Lin G.-Q. Tetrahedron Lett. 2009; 50: 3381

For selected examples, see:
• 8a Concellón JM, Pérez-Andrés JA, Rodríguez-Solla H. Angew. Chem. Int. Ed. 2000; 39: 2773
• 8b Concellón JM, Pérez-Andrés JA, Rodríguez-Solla H. Chem.–Eur. J. 2001; 7: 3062
• 8c Concellón JM, Bernad PL, Bardales E. Org. Lett. 2001; 3: 937
• 8d Concellón JM, Bardales E. Org. Lett. 2002; 4: 189
• 8e Concellón JM, Solla HR, Simal C, Huerta M. Org. Lett. 2005; 7: 5833