Modular Synthesis of Chiral N-Protected β-Seleno Amines and Amides via Cleavage of 2-Oxazolidinones and Application in Palladium-Catalyzed Asymmetric­ Allylic Alkylation

Abstract

A set of chiral β-seleno amines have been efficiently synthesized via the ring-opening reaction of chiral N-acyl oxazolidin­ones by selenium nucleophiles. These compounds could be transformed into β-seleno amides by reaction with acid chlorides. The present method is applicable to the synthesis of β-chalcogeno amides containing selenium, sulfur and tellurium atoms in good yields. Additionally, these new compounds were evaluated as ligands in the palladium-catalyzed asymmetric allylic alkylation, giving the corresponding alkylated products in up to 98% ee.

Key words

β-seleno amines - allylic alkylation - oxazolidinone ring-opening - asymmetric catalysis

References

• 1a Nicolaou KC. Petasis NA. In Selenium in Natural Products Synthesis   CIS, Inc.; Pennsylvania: 1984. and references therein
• 1b Klayman DL. Günter WHH. In Organoselenium Compounds: Their Chemistry and Biology   Wiley-Interscience; New York: 1973. 
• 1c Mugesh G. du Mont W.-W. Sies H. Chem. Rev.  2001,  101:  2125 
• 1d Nogueira CW. Zeni G. Rocha JBT. Chem. Rev.  2004,  104:  6255 
• 2a Paulmier C. Selenium Reagents and Intermediates in Organic Synthesis   Pergamon; Oxford, U.K.: 1986. 
• 2b Krief A. Hevesi L. Organoselenium Chemistry I   Springer; Berlin: 1988. 
• 2c Comasseto JV. Ling LW. Petragnani N. Stefani HA. Synthesis  1997,  373 
• 2d Braga AL. Reckziegel A. Silveira CC. Comasseto JV. Synth. Commun.  1994,  24:  1165 
• 2e Organoselenium Chemistry: A Practical Approach   Back TG. Oxford University Press; U.K.: 1999. 
• 3a Kumar Y. Green R. Borysko KZ. Wise DS. Wotring LL. Townsend LB. J. Med. Chem.  1993,  36:  3843 
• 3b Soriano-Garcia M. Curr. Med. Chem.  2004,  11:  1657 
• 3c de Silva V. Woznichak MM. Burns KL. Grant KB. May SW. J. Am. Chem. Soc.  2004,  126:  2409 
• 4a Wirth T. Tetrahedron  1999,  55:  1 
• 4b Wirth T. Angew. Chem. Int. Ed.  2000,  39:  3740 
• 4c Topics in Current Chemistry: Organoselenium Chemistry, Modern Developments in Organic Synthesis   Wirth T. Springer; Berlin: 2000. 
• 5a Gabriele B. Plastina P. Salerno G. Mancuso R. Costa M. Org. Lett.  2007,  9:  3319 
• 5b Ella-Menye J.-R. Wang G. Tetrahedron  2007,  63:  10034 
• 6a Matsunaga H. Ishizuka T. Kunieda T. Tetrahedron  2005,  61:  8073 
• 6b Ager DJ. Prakash I. Schaad DR. Chem. Rev.  1996,  96:  835 
• 7a Mukhtar TA. Wright GD. Chem. Rev.  2005,  105:  529 
• 7b Barbachyn MR. Ford CW. Angew. Chem. Int. Ed.  2003,  42:  2010 
• 7c Hutchinson DK. Curr. Top. Med. Chem.  2003,  3:  1021 
• 8a Hishibashi H. Uegaki M. Sakai M. Synlett  1997,  915 
• 8b Hishibashi H. Uegaki M. Sakai M. Takeda Y. Tetrahedron  2001,  57:  2115 
• 8c Kreisberg JD. Magnus P. Shinde S. Tetrahedron Lett.  2002,  43:  7393 
• 8d Poindexter GS. Owens DA. Dolan PL. Woo EJ. J. Org. Chem.  1992,  57:  6357 
• For reviews, see:
• 9a Braga AL. Lüdtke DS. Vargas F. Braga RC. Synlett  2006,  145 
• 9b Braga AL. Lüdtke DS. Vargas F. Curr. Org. Chem.  2006,  10:  1921 
• 10a Wirth T. Tetrahedron Lett.  1995,  36:  7849 
• 10b Santi C. Wirth T. Tetrahedron: Asymmetry  1999,  10:  1019 
• 10c Braga AL. Rodrigues OED. Paixão MW. Appelt HR. Silveira CC. Bottega DP. Synthesis  2002,  2338 
• 10d Braga AL. Paixão MW. Lüdtke DS. Silveira CC. Rodrigues OED. Org. Lett.  2003,  5:  2635 
• 11a Braga AL. Silva SJN. Lüdtke DS. Drekener RL. Silveira CC. Rocha JBT. Wessjohann LA. Tetrahedron Lett.  2002,  43:  7329 
• 11b Shi M. Wang C.-J. Zhang W. Chem. Eur. J.  2004,  10:  5507 
• 12a Sprinz J. Kiefer M. Helmchen G. Reggelin M. Huttner G. Walter O. Zsolnai L. Tetrahedron Lett.  1994,  35:  1523 
• 12b Hiroi K. Suzuki Y. Abe I. Tetrahedron: Asymmetry  1999,  10:  1173 
• 12c You S.-L. Hou X.-L. Dai L.-X. Tetrahedron: Asymmetry  2000,  11:  1495 
• 12d Hou X.-L. Wu X.-W. Dai L.-X. Cao B.-X. Sun J. Chem. Commun.  2000,  1195 
• 12e Braga AL. Paixão MW. Marin G. Synlett  2005,  1675 
• 12f Braga AL. Lüdtke DS. Sehnem JA. Alberto EE. Tetrahedron  2005,  61:  11664 
• 12g Braga AL. Lüdtke DS. Alberto EE. J. Braz. Chem. Soc.  2006,  17:  11 
• 12h Blajet MZ. Siedlecka R. Skarzewski J. Tetrahedron: Asymmetry  2007,  18:  131 
• 13a Tsuji J. Palladium Reagents and Catalysis, Innovations in Organic Synthesis   Wiley; New York: 1995. 
• 13b Trost BM. Van Vranken DL. Chem. Rev.  1996,  96:  395 
• 13c Trost BM. Lee C. Catalytic Asymmetric Synthesis   Ojima I. Wiley-VCH; New York: 2000.  2nd ed.; Chap. 8E. p.503 
• 14 Trost BM. Crawley ML. Chem. Rev.  2003,  103:  2921 
• 15a Braga AL. Vargas F. Sehnem JA. Braga RC. J. Org. Chem.  2005,  70:  9021 
• 15b Braga AL. Vargas F. Sehnem JA. Wessjohann LA. Eur. J. Org. Chem.  2006,  4993 
• 16 Crimmins MT. King BW. Tabet EA. Chaughary K. J. Org. Chem.  2001,  66:  894 
• 17 Gladysz JA. Hornby JL. Garbe JE. J. Org. Chem.  1978,  43:  1204