A General Procedure for theOne-pot Preparation of Polyfunctionalized Nitrocyclopropanes

Roberto Ballini; Dennis Fiorini; Alessandro Palmieri

doi:10.1055/s-2003-40985

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2003(11): 1704-1706
DOI: 10.1055/s-2003-40985

LETTER

A General Procedure for theOne-pot Preparation of Polyfunctionalized Nitrocyclopropanes

Roberto Ballini*, Dennis Fiorini, Alessandro Palmieri
Dipartimento di Scienze Chimiche dell’Università diCamerino, Via S. Agostino 1, 62032 Camerino, Italy
Fax: +39(0737)402297; e-Mail: roberto.ballini@unicam.it;

Further Information

Publication History

Received 28 May 2003
Publication Date:
05 August 2003 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Nitrocyclopropane formation has been successfully carried outby reaction of bromonitromethane with electrophilic alkenes bearingtwo electron-withdrawing groups in the α- and β-positions,and in the presence of potassium carbonate as base. The method allowsgood yields and moderate to satisfactory diastereoselectivity withlinear alkenes, while shows the complete formation of the exo-product with N-alkylmaleimides.

Key words

nitrocyclopropanes - bromonitromethane - potassium carbonate - one-pot preparation - Michael reaction

References

1a Elliot M. SyntheticPyretroids ACS Symposium Series 87, AmericanChemical Society; Washington D. C.: 1977.

Google Scholar
1b Corey EJ. Achiwa K. Katzenellenbogen JA. J. Am. Chem. Soc. 1969, 91: 4318

Google Scholar
1c Higgs MD. Mulheirn LJ. Tetrahedron 1981, 37: 4259

Google Scholar
1d Paul VJ. Fenical W. Science 1983, 221: 747

Google Scholar
1e Kerr RG. Baker B. J. Nat. Prod.Rep. 1991, 465

Google Scholar
1f Williams RM. Fegley GJ. J. Am.Chem. Soc. 1991, 113: 8796

Google Scholar
1g Yoshida M. Kohsaka M. Horikoshi K. J.Antibiotics 1990, 43: 748

Google Scholar
2a Martin SF. Austin RE. Oalmann CJ. Tetrahedron Lett. 1990, 31: 4731

Crossref Google Scholar
2b Walsh C. Tetrahedron 1982, 38: 871

Crossref Google Scholar
2c Worbeck DW. Sham HL. Herrin T. Rosenbrook W. Plattner JJ. J. Chem. Soc., Chem. Commun. 1992, 128

Crossref Google Scholar
3a Zindel J. Zeeck A. Hönlg WA. de Meijere A. TetrahedronLett. 1993, 34: 1917

Article in Thieme Connect Google Scholar
3b Braish TF. Castaldi M. Chan S. Fox DE. Keltonic T. McGarry J. Hawkins JM. Norris T. Rose PR. Sieser JE. Sitter BJ. Watson H. Synlett 1996, 1100

Article in Thieme Connect Google Scholar
3c Brandl M. Kokhushkov SI. Loscha K. Kokoreva OV. Yufit DS. Howard JAK. Synlett 2000, 1741

Article in Thieme Connect Google Scholar
4a Seebach D. Colvin EW. Lehr F. Weller T. Chimia 1979, 33: 1

Article in Thieme Connect Google Scholar
4b Rosini G. Ballini R. Synthesis 1988, 833

Article in Thieme Connect Google Scholar
4c Rosini G. Ballini R. Petrini M. Marotta E. Righi P. Org.Prep. Proced. Int. 1990, 22: 707

Article in Thieme Connect Google Scholar
4d Ballini R. Synlett 1999, 1009

Article in Thieme Connect Google Scholar
4e Ono N. The Nitro Group in Organic Synthesis JohnWiley; New York: 2001.

Article in Thieme Connect Google Scholar
5a O’Bannon PE. Dailey WP. J. Org. Chem. 1990, 55: 353

Google Scholar
5b Kay Y. Knochel P. Kwiatkowski S. Dunitz JD. Oth JFM. Seebach D. Helv. Chim.Acta 1982, 65: 137

Google Scholar
5c Kocór M. Kroszczyski W. Synthesis 1976, 813

Google Scholar
5d Galley G. Hübner J. Anklam S. Tones PG. Pätzel M. TetrahedronLett. 1996, 37: 6307

Google Scholar
5e Hübner J. Liebscher J. Pätzel M. Tetrahedron 2002, 58: 10485

Google Scholar
5f Yu J. Falck JR. J. Org. Chem. 1992, 57: 3757

Google Scholar
5g Snider BB. Che Q. Tetrahedron 2002, 58: 7821

Google Scholar
5h Larionov OV. Savel’era T. Kochetkov KA. Ikonnokov NS. Kozhushkov SI. Yufit DS. Howard JAK. Khrustalev VN. Belokon YN. De Meijere A. Eur.J. Org. Chem. 2003, 869

Google Scholar
6 Norris T. Braish TF. Butters M. DeVries KM. Hawkins JM. Massett SS. Rose PR. Santafianos D. Sklavounos C. J. Chem. Soc., Perkin Trans.1 2000, 1615

Google Scholar
7a Ballini R. Rinaldi A. TetrahedronLett. 1994, 35: 9247

Google Scholar
7b Ballini R. Bosica G. Tetrahedron 1995, 51: 4213

Google Scholar
7c Ballini R. Bosica G. Fiorini D. Gil MV. Petrini M. Org.Lett. 2001, 3: 1265

Google Scholar
8a Ballini R. Barboni L. Bosica G. Petrini M. Synlett 2000, 391

Article in Thieme Connect Google Scholar
8b Ballini R. Bosica G. Petrelli L. Petrini M. Synthesis 1999, 1236

Article in Thieme Connect Google Scholar
8c Ballini R. Marcantoni E. Perella S. J.Org. Chem. 1999, 64: 2954

Article in Thieme Connect Google Scholar
8d Ballini R. Bosica G. Masè A. Petrini M. Eur. J. Org. Chem. 2000, 2927

Article in Thieme Connect Google Scholar
8e Ballini R. Bosica G. Fiorini D. Giarlo G. Synthesis 2001, 2003

Article in Thieme Connect Google Scholar
8f Ballini R. Bosica G. Fiorini D. Righi P. Synthesis 2002, 681

Article in Thieme Connect Google Scholar
9 The compound 2a hasbeen prepared previously: Dominguez C. Czàky AG. Plumet J. TetrahedronLett. 1990, 31: 7669

Crossref Google Scholar
10 The compounds 2b,c havebeen prepared previously: Kitano H. Minami S. Morita T. Matsumoto K. Hatanaka M. Synthesis 2002, 739

Article in Thieme Connect Google Scholar

11

Selected analytical data for the compounds 3h-j. 3h: White solid, mp 132-134 °C.IR: 1710, 1552 cm^-1; ¹HNMR (CDCl₃): δ = 2.92 (s, 3 H), 3.39(d, 2 H, J = 1.4 Hz), 4.65 (t, 1H, J = 1.6 Hz); ¹³CNMR (CDCl₃): δ = 25.1, 27.7, 62.6, 168.9;EIMS (70 eV) m/z: 170 (M⁺),96, 39. Anal. Calcd. For C₆H₆N₂O₄ (170.12):C, 42.36; H, 3.55; N, 16.47. Found: C, 42.52; H, 3.64; N, 16.38. 3i: White solid, mp 124-126 °C. IR:1716, 1547 cm^-1; ¹HNMR (CDCl₃): δ = 1.14 (t, 3 H, J = 7.2 Hz), 3.38 (d, 2 H, J = 1.5 Hz), 3.48 (q, 2 H, J = 7.3 Hz), 4.59 (t, 1 H, J = 1.6 Hz); ¹³CNMR (CDCl₃): δ = 13.0, 27.6, 34.2,62.6, 168.6; EIMS (70 eV) m/z:184 (M⁺), 169, 95, 39. Anal. Calcd For C₇H₈N₂O₄ (184.15):C, 45.66; H, 4.38; N, 15.21. Found: C, 45.55; H, 4.46; N, 15.14. 3j: White solid, mp 158-160 °C.IR: 1709, 1557 cm^-1; ¹HNMR (CDCl₃):
δ = 1.50 (s,9 H), 3.25 (d, 2 H, J = 1.4Hz), 4.51 (t, 1 H, J = 1.4 Hz); ¹³CNMR (CD₃COCD₃): δ = 29.5,29.9, 30.3, 63.1, 171.2; EIMS (70 eV) m/z:212 (M⁺), 197, 157, 95, 56, 39. Anal. CalcdFor C₉H₁₂N₂O₄ (212.20):C, 50.94; H, 5.79; N, 13.20. Found: C, 60.06; H, 5.59; N, 13.11.