Oxazoline-Thiourea as a Bifunctional Organocatalyst: Enantioselective aza-Henry Reactions

Yu-wei Chang; Jing-jun Yang; Jin-ning Dang; Yue-xia Xue

doi:10.1055/s-2007-984916

LETTER

Oxazoline-Thiourea as a Bifunctional Organocatalyst: Enantioselective aza-Henry Reactions

Yu-wei Chang*^a, Jing-jun Yang^a, Jin-ning Dang^a, Yue-xia Xue^b
^a Department of Chemistry, Hezuo Minorities Teachers’ College, Hezuo 747000, P. R. of China
Fax: +86(941)8252686; e-Mail: changyuwei@hzmtc.edu.cn;
^b Yizheng Chemical Fiber Co, Ltd Chemical Plant, Yangzhou 211900, P. R. of China

Abstract

All articles of this category

Abstract

Bifunctional oxazoline-thiourea-based organocatalysts were synthesized and applied to the aza-Henry reactions between N-Boc aryl imines and nitromethane in high ee and chemical yields at room temperature.

Key words

oxazoline - thiourea - aza-Henry reactions - organocatalyst

Full Text

References

References and Notes

<A NAME="RW05207ST-1">1</A> Westermann B. Angew. Chem. Int. Ed. 2003, 42: 151

<A NAME="RW05207ST-2">2</A> Lucet D. Le Gall T. Mioskowski C. Angew. Chem. Int. Ed. 1998, 37: 2580

<A NAME="RW05207ST-3A">3a</A> O’Brien PH. Sliskovic DR. Blankley CJ. Roth B. Wilson MW. Hamelehle KL. Krause BR. Stanfield RL. J. Med. Chem. 1994, 37: 1810

<A NAME="RW05207ST-3B">3b</A> Adams H. Anderson JC. Peace S. Pennell AMK. J. Org. Chem. 1998, 63: 9932

<A NAME="RW05207ST-4A">4a</A> Pinnick HW. Org. React. 1990, 38: 655

<A NAME="RW05207ST-4B">4b</A> Ballini R. Petrini M. Tetrahedron 2004, 60: 1017

<A NAME="RW05207ST-4C">4c</A> Foresti E. Palmieri G. Petrini M. Profeta R. Org. Biomol. Chem. 2003, 1: 4275

<A NAME="RW05207ST-5A">5a</A> Yamada K. Harwood SJ. Gröger H. Shibasaki M. Angew. Chem. Int. Ed. 1999, 38: 3504

<A NAME="RW05207ST-5B">5b</A> Yamada K. Moll G. Shibasaki M. Synlett 2001, 980

<A NAME="RW05207ST-6A">6a</A> Knudsen KR. Risgaard T. Nishiwaki N. Gothelf KV. Jørgensen KA. J. Am. Chem. Soc. 2001, 123: 5843

<A NAME="RW05207ST-6B">6b</A> Nishiwaki N. Knudsen KR. Gothelf KV. Jørgensen KA. Angew. Chem. Int. Ed. 2001, 40: 2992

<A NAME="RW05207ST-6C">6c</A> Knudsen KR. Jørgensen KA. Org. Biomol. Chem. 2005, 3: 1362

<A NAME="RW05207ST-7">7</A> Palomo C. Oiarbide M. Halder R. Laso A. López R. Angew. Chem. Int. Ed. 2006, 45: 117

<A NAME="RW05207ST-8A">8a</A> Dalko PI. Moisan L. Angew. Chem. Int. Ed. 2001, 40: 3726

<A NAME="RW05207ST-8B">8b</A> Dalko PI. Moisan L. Angew. Chem. Int. Ed. 2004, 43: 5138

<A NAME="RW05207ST-9A">9a</A> Okino T. Nakamura S. Furukawa T. Takemoto Y. Org. Lett. 2004, 6: 625

<A NAME="RW05207ST-9B">9b</A> Xu X. Furukawa T. Okino T. Miyabe H. Takemoto Y. Chem. Eur. J. 2006, 12: 466

<A NAME="RW05207ST-10">10</A> Yoon TP. Jacobsen EN. Angew. Chem. Int. Ed. 2005, 44: 466

<A NAME="RW05207ST-11A">11a</A> Bordwell FG. Ji G. J. Am. Chem. Soc. 1991, 113: 8398

<A NAME="RW05207ST-11B">11b</A> Kelly TR. Kim MH. J. Am. Chem. Soc. 1994, 116: 7072

<A NAME="RW05207ST-12">12</A> Reddy LR. Saravanan P. Corey EJ. J. Am. Chem. Soc. 2004, 126: 6230

<A NAME="RW05207ST-13">13</A> Demko ZP. Sharpless KB. Org. Lett. 2002, 4: 2525

Representative Procedure To a stirred solution of N-Boc phenyl imines (1 mmol) and the catalyst (0.1 mmol) in THF (2 mL) was added MeNO₂ (10 mmol), and the mixture was stirred for 24 h at r.t. Then the reaction mixture was condensed under reduced pressure, and the obtained residue was purified by column chromatog-raphy on silica gel to afford desired product 6a (93% yield).