Chiral Phosphoric Acid Catalyzed Stereoselective Spiroketalizations

Pavel Nagorny; Zhankui Sun; Grace A. Winschel

doi:10.1055/s-0032-1318098

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(6): 661-665
DOI: 10.1055/s-0032-1318098

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Chiral Phosphoric Acid Catalyzed Stereoselective Spiroketalizations

Pavel Nagorny*

Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI 48109, USA Fax: +1(734)6474865 eMail: nagorny@umich.edu

,

Zhankui Sun

Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI 48109, USA Fax: +1(734)6474865 eMail: nagorny@umich.edu

,

Grace A. Winschel

Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI 48109, USA Fax: +1(734)6474865 eMail: nagorny@umich.edu

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Abstract

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Abstract

The spiroketal functionality is an important structural motif present in numerous natural products. The synthesis of chiral spiroketals is typically achieved under equilibrating conditions and only few asymmetric approaches are known. We have demonstrated that chiral phosphoric acids (CPAs) could serve as effective catalysts for enantioselective spiroketalizations as well as control the course of the corresponding diastereoselective reactions.

Key words

acetals - spiro compounds - asymmetric catalysis - oxocarbenium ion - enantioselectivity - diastereoselectivity - chiral phosphoric acids

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Referenzen

References
1 Perron F, Albizati KF. Chem. Rev. 1989; 89: 1617

2a Mitsuhashi S, Shima H, Kawamura T, Kikuchi K, Oikawa M, Ichihara A, Oikawa H. Bioorg. Med. Chem. Lett. 1999; 9: 2007
2b Uckun FM, Mao C, Vassilev AO, Huang H, Jan S.-T. Bioorg. Med. Chem. Lett. 2000; 10: 541
2c Huang H, Mao C, Jan S.-T, Uckun FM. Tetrahedron Lett. 2000; 41: 1699

3a Boivin TL. B. Tetrahedron 1987; 43: 3309
3b Mead KT, Brewer BN. Curr. Org. Chem. 2003; 7: 227
3c Aho JE, Pihko PM, Rissa TK. Chem. Rev. 2005; 105: 4406
3d Favre S, Vogel P, Gerber-Lemaire S. Molecules 2008; 13: 2570
3e El Sous M, Ganame D, Zanatta S, Rizzacasa M. ARKIVOC 2006; (vii): 105

4 Deslongchamps P, Rowan DD, Pothier N, Sauve G, Saunders JK. Can. J. Chem. 1981; 59: 1105

5a Gallimore AR, Stark CB. W, Bhatt A, Harvey BM, Demydchuk Y, Bolanos-Garcia V, Fowler DJ, Staunton J, Leadlay PF, Spencer JB. Chem. Biol. 2006; 13: 453
5b Takahashi S, Toyoda A, Sekiyama Y, Takagi H, Nogawa T, Uramoto M, Suzuki R, Koshino H, Kumano T, Panthee S, Dairi T, Ishikawa J, Ikeda H, Sakaki Y, Osada H. Nat. Chem. Biol. 2011; 7: 461

6a Negri DP, Kishi Y. Tetrahedron Lett. 1987; 28: 1063
6b Paterson I, Wallace DJ, Gibson KR. Tetrahedron Lett. 1997; 38: 8911
6c Wardrop DJ, Zhang W, Fritz J. Org. Lett. 2002; 4: 489
6d Holson EB, Roush WR. Org. Lett. 2002; 4: 3719
6e Pihko PM, Aho JE. Org. Lett. 2004; 6: 3849
6f Potuzak JS, Moilanen SB, Tan DS. J. Am. Chem. Soc. 2005; 127: 13796
6g Takaoka LR, Buckmelter AJ, LaCruz TE, Rychnovsky SD. J. Am. Chem. Soc. 2005; 127: 528
6h Moilanen SB, Potuzak JS, Tan DS. J. Am. Chem. Soc. 2006; 128: 1792
6i Vellucci D, Rychnovsky SD. Org. Lett. 2007; 9: 711
6j Castagnolo D, Breuer I, Pihko PM. J. Org. Chem. 2007; 72: 10081
6k Liu G, Wurst JM, Tan DS. Org. Lett. 2009; 11: 3670

7 Wurst JM, Liu G, Tan DS. J. Am. Chem. Soc. 2011; 133: 7916

8a Iwata C, Hattori K, Uchida S, Imanishi T. Tetrahedron Lett. 1984; 25: 2995
8b Iwata C, Fujita M, Hattori K, Uchida S, Imanishi T. Tetrahedron Lett. 1985; 26: 2221
8c Uchiyama M, Oka M, Harai S, Ohta A. Tetrahedron Lett. 2001; 42: 1931
8d Wu K.-L, Wilkinson S, Reich NO, Pettus TR. R. Org. Lett. 2007; 9: 5537

9 Beaver MG, Woerpel KA. J. Org. Chem. 2010; 75: 1107
10 Coric I, List B. Nature (London) 2012; 483: 315
11 Sun Z, Winschel GA, Borovika A, Nagorny P. J. Am. Chem. Soc. 2012; 134: 8074
12 Pothier N, Goldstein S, Deslongchamps P. Helv. Chim. Acta 1992; 75: 604
13 Borovika A, Nagorny P. J. Carbohydr. Chem. 2012; 31: 255
14 Young PR, Jencks WP. J. Am. Chem. Soc. 1977; 99: 8232

15a Simon L, Goodman JM. J. Org. Chem. 2010; 75: 589
15b Simon L, Goodman JM. J. Org. Chem. 2011; 76: 1775
15c Fleischmann M, Drettwan D, Sugiono E, Rueping M, Gschwind RM. Angew. Chem. Int. Ed. 2011; 50: 1

16 Winschel, G.; Nagorny, P. unpublished work.