Synthesis of New Enantiomerically Pure Organoiodine Catalysts and Their Application in the α-Functionalization of Ketones

Abstract

The synthesis of enantiomerically pure iodoarenes and their application to the α-oxysulfonylation of propiophenone, and the lactonization of 5-oxo-5-phenylpentanoic acid using MCPBA as stoichiometric oxidant are reported to give useful synthetic intermediates in good yields and moderate enantioselectivities.

hypervalent iodine reagents - organocatalysis - oxidation - stereoselective synthesis

References

Reviews:

1a Varvoglis A. The Organic Chemistry of Polycoordinated Iodine   VCH; Weinheim: 1992. 

1b Varvoglis A. Hypervalent Iodine in Organic Synthesis   Academic Press; London: 1997. 

1c Finet J. Ligand Coupling Reactions with Heteroatomic Compounds   Pergamon; Oxford: 1998. 

1d Zhdankin VV. Stang PJ. Tetrahedron  1998,  55:  10927 

1e Wirth T. Hirt UH. Synthesis  1999,  1271 

1f Ochiai M. In Chemistry of Hypervalent Compounds   Akiba K. VCH; New York: 1999.  p.359 

1g Zhdankin VV. Stang PJ. Chem. Rev.  2002,  102:  2523 

1h Wirth T. Hypervalent Iodine Chemistry   Springer; Berlin: 2003. 

1i Tohma H. Kita Y. Adv. Synth. Catal.  2004,  346:  111 

1j Wirth T. Angew. Chem. Int. Ed.  2005,  44:  3656 ; Angew. Chem. 2005, 117: 3722

1k Zhdankin VV. In Science of Synthesis   Vol. 31a:  Ramsden C. Thieme; Stuttgart: 2007.  Chap. 31.4.1. p.161 

1l Zhdankin VV. Stang PJ. Chem. Rev.  2008,  108:  5299 

2 Braddock DC. Cansell G. Hermitage SA. Chem. Commun.  2006,  2483 

3 Rebrovic L. Koser GF. J. Org. Chem.  1984,  49:  2462 

4 Koser GF. Relenyi AG. Kalos AN. Rebrovic L. Wettach RH. J. Org. Chem.  1982,  47:  2487 

5a Altermann SM. Richardson RD. Page TK. Schmidt RK. Holland E. Mohammed U. Paradine SM. French AN. Richter C. Bahar AM. Witulski B. Wirth T. Eur. J. Org. Chem.  2008,  5315 

5b Shah AA. Khan ZA. Choudhary N. Lohölter C. Schäfer S. Marie GPL. Farooq U. Witulski B. Wirth T. Org. Lett.  2009,  11:  3578 

6a Wirth T. Hirt U. Tetrahedron: Asymmetry  1997,  8:  23 

6b Hirt UH. Springler B. Wirth T. J. Org. Chem.  1998,  63:  7674 

6c Hirt UH. Schuster MFH. French AN. Wiest OG. Wirth T. Eur. J. Org. Chem.  2001,  1569 

7 Richardson RD. Wirth T. Angew. Chem. Int. Ed.  2006,  45:  4402 ; Angew. Chem. 2006, 118, 4510

8 Fuchigami T. Fujita T. J. Org. Chem.  1994,  59:  7190 

9a Ochiai M. Takeuchi Y. Katayama K. Sueda T. Miyamoto K. J. Am. Chem. Soc.  2005,  127:  12244 

9b Ochiai M. Miyamoto K. Eur. J. Org. Chem.  2008,  4229 

10a Dohi T. Maruyama A. Yoshimura M. Morimoto K. Tohma H. Kita Y. Angew. Chem. Int. Ed.  2005,  44:  6193 ; Angew. Chem. 2005, 117, 6349

10b Dohi T. Kita Y. Chem. Commun.  2009,  2073 

11 Richardson RD. Page TK. Altermann SM. Paradine SM. French AN. Wirth T. Synlett  2007,  538 

12 Dohi T. Maruyama A. Takenaga N. Senami K. Minamitsuji Y. Fujioka H. Caemmerer SB. Kita Y. Angew. Chem. Int. Ed.  2008,  47:  3787 ; Angew. Chem. 2008, 120, 3847

13a Reisinger CM. Wang X. List B. Angew. Chem. Int. Ed.  2008,  47:  8112 ; Angew. Chem. 2008, 120, 8232

13b Marigo M. Jørgensen KA. Chem. Commun.  2006,  2001 

13c Momiyama N. Torii H. Saito S. Yamamoto H. Proc. Natl. Acad. Sci. U.S.A.  2004,  101:  5374 

13d Longbottom DA. Franckevicius V. Kumarn S. Oelke AJ. Wascholowski V. Ley SV. Aldrichimica Acta  2008,  41:  3 

14 Hassner A. Alexanian V. Tetrahedron Lett.  1978,  46:  4475 

15 Yamamoto Y. Togo H. Synlett  2006,  798 

16 Uyanik M. Yasui T. Ishihara K. Bioorg. Med. Chem. Lett.  2009,  19:  3848 

17 Boyd DR. Sharma ND. Smith AE. J. Chem. Soc., Perkin Trans. 1  1982,  2767 

18 The absolute configuration was determined by independent synthesis of 3 from (S)-(-)-lactic acid: Imfeld M. Suchy M. Vogt P. Kucác P. Schlageter M. Widmer E. Helv. Chim. Acta  1982,  65:  1233