Organocatalytic Highly
Enantioselective Mannich-Type Reactions of Fluoromalonate
with N-Boc-Aldimines

Ju Hee Lee; Dae Young Kim

doi:10.1055/s-0029-1218736

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml

Teilen / Bookmarken

Facebook X Linkedin Weibo

PDF herunterladen

Synthesis 2010(11): 1860-1864
DOI: 10.1055/s-0029-1218736

SPECIALTOPIC

Organocatalytic Highly Enantioselective Mannich-Type Reactions of Fluoromalonate with N-Boc-Aldimines

Ju Hee Lee, Dae Young Kim*
Department of Chemistry, Soonchunhyang University, Asan, Chungnam 336-745, Korea
Fax: +82(41)5301247; e-Mail: dyoung@sch.ac.kr;

Weitere Informationen

Publikationsverlauf

Received 28 February 2010
Publikationsdatum:
12. April 2010 (online)

Abstract
Volltext
Referenzen

Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

The catalytic enantioselective Mannich reaction promoted by chiral bifunctional organocatalysts is described. The treatment of diethyl fluoromalonate with N-Boc-aldimines under mild reaction conditions afforded the corresponding β-amino-β-fluoromalonates with excellent enantioselectivity (93-97% ee).

Key words

Mannich reaction - asymmetric catalysis - bifunctional organocatalyst - fluoromalonate - aldimines

References and Notes

1a Hudlicky M. Pavlath AE. Chemistry of Organic Fluorine Compounds II American Chemical Society; Washington DC: 1995.

Google Scholar
1b Kirk KLJ. J. Fluorine Chem. 2006, 127: 1013

Google Scholar
1c Isanobor C. O’Hagan D. J. Fluorine Chem. 2006, 127: 303

Google Scholar
1d Muller K. Faeh C. Diederich F. Science 2007, 317: 1881

Google Scholar
1e Kirk KL. Org. Process Res. Dev. 2008, 12: 305

Google Scholar
2a Purser S. Moore PR. Swallow S. Gouverneur V. Chem. Soc. Rev. 2008, 37: 320

Google Scholar
2b Hiyama T. Kanie K. Kusumoto T. Morizawa Y. Shimizu M. Organofluorine Compounds: Chemistry and Applications Springer Verlag; Berlin: 2000.

Google Scholar
3a Enantiocontrolled Synthesis of Fluoro-organic Compounds Soloshonok VA. John Wiley & Sons; Chichester: 1999.

Google Scholar
3b Bravo P. Resnati G. Tetrahedron: Asymmetry 1990, 1: 661

Google Scholar
3c Asymmetric Fluoroorganic Chemistry: Synthesis, Application, and Future Directions ACS Symposium Series 746: Ramachandran PV. American Chemical Society; Washington: 2000.

Google Scholar
For reviews, see:
4a Mikami K. Itoh Y. Yamanaka M. Chem. Rev. 2004, 104: 1

Google Scholar
4b Ibrahim H. Togni A. Chem. Commun. 2004, 1147

Google Scholar
4c Ma J.-A. Cahard D. Chem. Rev. 2008, 108: PR1

Google Scholar
4d France S. Weatherwax A. Lectka T. Eur. J. Org. Chem. 2005, 475

Google Scholar
4e Oestreich M. Angew. Chem. Int. Ed. 2005, 44: 2324

Google Scholar
4f Pihko PM. Angew. Chem. Int. Ed. 2006, 45: 544

Google Scholar
4g Prakash GKS. Beier P. Angew. Chem. Int. Ed. 2006, 45: 2172

Google Scholar
4h Bobbio C. Gouverneur V. Org. Biomol. Chem. 2006, 4: 2065

Google Scholar
4i Shibata N. Ishimaru T. Nakamura S. Toru T.
J. Fluorine Chem. 2007, 128: 469

Google Scholar
4j Brunet VA. O’Hagan D. Angew. Chem. Int. Ed. 2008, 47: 1179

Google Scholar
4k Smits R. Cadicamo CD. Burger K. Koksch B. Chem. Soc. Rev. 2008, 37: 1727

Google Scholar
For recent selected examples of catalytic asymmetric fluorinations of active methines, see:
5a Hintermann L. Togni A. Angew. Chem. Int. Ed. 2000, 39: 4359

Google Scholar
5b Kim DY. Park EJ. Org. Lett. 2002, 4: 545

Google Scholar
5c Hamashima Y. Yagi K. Takano H. Tamás L. Sodeoka M. J. Am. Chem. Soc. 2002, 124: 14530

Google Scholar
5d Ma J.-A. Cahard D. Tetrahedron: Asymmetry 2004, 15: 1007

Google Scholar
5e Shibata N. Ishimaru T. Nagai T. Kohno J. Toru T. Synlett 2004, 1703

Google Scholar
5f Bernardi L. Jørgensen KA. Chem. Commun. 2005, 1324

Google Scholar
5g Kim SM. Kim HR. Kim DY. Org. Lett. 2005, 7: 2309

Google Scholar
5h Kim HR. Kim DY. Tetrahedron Lett. 2005, 46: 3115

Google Scholar
5i Ishimaru T. Shibata N. Horikawa T. Yasuda N. Nakamura S. Toru T. Shiro M. Angew. Chem. Int. Ed. 2008, 47: 4157

Google Scholar
5j Lee NR. Kim SM. Kim DY. Bull. Korean Chem. Soc. 2009, 30: 829

Google Scholar
For asymmetric Michael-type reactions of α-fluoro-malonates, see:
6a Kim DY. Kim SM. Koh KO. Mang JY. Bull. Korean Chem. Soc. 2003, 24: 1425

Google Scholar
6b Nichols PJ. DeMattei JA. Barnett BR. LeFur NA. Chuang T.-H. Piscopio AD. Koch K. Org. Lett. 2006, 8: 1495

Google Scholar
6c Kwon BK. Kim SM. Kim DY.
J. Fluorine Chem. 2009, 130: 759

Google Scholar
6d Companyo X. Hejnova M. Kamlar M. Vesely J. Moyano A. Rios R. Tetrahedron Lett. 2009, 50: 5051

Google Scholar
For asymmetric Michael-type reactions of α-fluoro-β-keto esters, see:
7a Nakamura M. Hajra A. Endo K. Nakamura E. Angew. Chem. Int. Ed. 2005, 44: 7248

Google Scholar
7b He R. Wang X. Hashimoto T. Maruoka K. Angew. Chem. Int. Ed. 2008, 47: 9466

Google Scholar
7c Mang JY. Kwon DG. Kim DY. J. Fluorine Chem. 2009, 130: 259

Google Scholar
7d Han X. Luo J. Liu C. Lu Y. Chem. Commun. 2009, 2044

Google Scholar
7e Li H. Zhang S. Yu C. Song X. Wang W. Chem. Commun. 2009, 2136

Google Scholar
7f Oh Y. Kim SM. Kim DY. Tetrahedron Lett. 2009, 50: 4674

Google Scholar
8a Fukuzumi T. Shibata N. Sugiura M. Yasui H. Nakamura S. Toru T. Angew. Chem. Int. Ed. 2006, 45: 4973

Google Scholar
8b Mizuta S. Shibata N. Goto Y. Furukawa T. Nakamura S. Toru T. J. Am. Chem. Soc. 2007, 129: 6394

Google Scholar
8c Furukawa T. Shibata N. Mizuta S. Nakamura S. Toru T. Shiro M. Angew. Chem. Int. Ed. 2008, 47: 8051

Google Scholar
8d Moon HW. Cho MJ. Kim DY. Tetrahedron Lett. 2009, 50: 4896

Google Scholar
8e Furukawa T. Goto Y. Kawazoe J. Tokunaga E. Nakamura S. Yang Y. Du H. Kakehi A. Shiro M. Shibata N. Angew. Chem. Int. Ed. 2010, 49: 1642

Google Scholar
For selected recent reviews, see:
9a Verkade JMM. van Hemert LJC. Quaedflieg PJLM. Rutjes FPJT. Chem. Soc. Rev. 2008, 37: 29

Google Scholar
9b Ting A. Schaus SE. Eur. J. Org. Chem. 2007, 5797

Google Scholar
9c Marques MMB. Angew. Chem. Int. Ed. 2006, 45: 348

Google Scholar
9d Cordova A. Acc. Chem. Res. 2004, 37: 102

Google Scholar
Selected examples of Mannich-type reactions of enolates, see:
10a Sikert M. Schneider C. Angew. Chem. Int. Ed. 2008, 47: 3631

Google Scholar
10b Itoh J. Fuchibe K. Akiyama T. Synthesis 2008, 1319

Google Scholar
10c Kobayashi S. Yazaki R. Seki K. Ueno M. Tetrahedron 2007, 63: 8425

Google Scholar
10d Saruhashi K. Kobayashi S. J. Am. Chem. Soc. 2006, 128: 11232

Google Scholar
10e Kobayashi S. Ueno M. Saito S. Mizuki Y. Ishitani H. Yamashita Y. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5476

Google Scholar
10f Akiyama T. Itoh J. Yokota K. Fuchibe K. Angew. Chem. Int. Ed. 2004, 43: 1566

Google Scholar
10g Wenzel AG. Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 12964

Google Scholar
11a Hamashima Y. Sasamoto N. Umebayashi N. Sodeoka M. Chem. Asian J. 2008, 3: 1443

Google Scholar
11b Chen Z. Morimoto H. Matsunaga S. Shibasaki M. J. Am. Chem. Soc. 2008, 130: 2170

Google Scholar
11c Kobayashi S. Gustafsson T. Shimizu Y. Kiyohara H. Matsubara R. Org. Lett. 2006, 8: 4923

Google Scholar
11d Hamashima Y. Sasamoto N. Hotta D. Somei H. Umebayashi N. Sodeoka M. Angew. Chem. Int. Ed. 2005, 44: 1525

Google Scholar
11e Kang YK. Kim DY. J. Org. Chem. 2009, 74: 5734

Google Scholar
11f Kim EJ. Kang YK. Kim DY. Bull. Korean Chem. Soc. 2009, 30: 1437

Google Scholar
11g Lee JH. Kim DY. Adv. Synth. Catal. 2009, 351: 1779

Google Scholar
12a Puglisi A. Benaglia M. Annunziata R. Rossi D. Tetrahedron: Asymmetry 2008, 19: 2258

Google Scholar
12b Fini F. Bernardi L. Herrera RP. Pettersen D. Ricci A. Sgarzani V. Adv. Synth. Catal. 2006, 348: 2043

Google Scholar
12c Yamaoka Y. Miyabe H. Yasui Y. Takemoto Y. Synthesis 2007, 2571

Google Scholar
12d Tillman AL. Ye J. Dixon DJ. Chem. Commun. 2006, 1191

Google Scholar
13a Kim DY. Huh SC. Kim SM. Tetrahedron Lett. 2001, 42: 6299

Google Scholar
13b Kim DY. Huh SC. Tetrahedron 2001, 57: 8933

Google Scholar
13c Park EJ. Kim MH. Kim DY.
J. Org. Chem. 2004, 69: 6897

Google Scholar
13d Kang YK. Kim DY. Tetrahedron Lett. 2006, 47: 4265

Google Scholar
13e Kang YK. Cho MJ. Kim SM. Kim DY. Synlett 2007, 1135

Google Scholar
13f Cho MJ. Kang YK. Lee NR. Kim DY. Bull. Korean Chem. Soc. 2007, 28: 2191

Google Scholar
13g Kim SM. Kang YK. Cho MJ. Mang JY. Kim DY. Bull. Korean Chem. Soc. 2007, 28: 2435

Google Scholar
13h Lee JH. Bang HT. Kim DY. Synlett 2008, 1821

Google Scholar
13i Mang JY. Kim DY. Bull. Korean Chem. Soc. 2008, 29: 2091

Google Scholar
13j Kang YK. Kim DY. Bull. Korean Chem. Soc. 2008, 29: 2093

Google Scholar
13k Kim DY. Bull. Korean Chem. Soc. 2008, 29: 2036

Google Scholar
13l Mang JY. Kwon DG. Kim DY. Bull. Korean Chem. Soc. 2009, 30: 249

Google Scholar
14a Kim SM. Lee JH. Kim DY. Synlett 2008, 2659

Google Scholar
14b Jung SH. Kim DY. Tetrahedron Lett. 2008, 49: 5527

Google Scholar
15 Ye J. Dixon DJ. Hynes PS. Chem. Commun. 2005, 4481

Crossref Google Scholar
16 Thenappen A. Burton DJ. J. Org. Chem. 1991, 56: 273

Crossref Google Scholar