Asymmetric Cyclopropanations and Cycloadditions of Dioxocarbenes

Paul Müller; Yves F. Allenbach; Sabrina Chappellet; Ashraf Ghanem

doi:10.1055/s-2006-926452

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-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2006(10): 1689-1696
DOI: 10.1055/s-2006-926452

SPECIALTOPIC

Asymmetric Cyclopropanations and Cycloadditions of Dioxocarbenes

Paul Müller*, Yves F. Allenbach, Sabrina Chappellet, Ashraf Ghanem
Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, 1211 Geneva 4, Switzerland
Fax: +41(22)3793215; e-Mail: paul.muller@chiorg.unige.ch;

Further Information

Publication History

Received 16 February 2006
Publication Date:
27 April 2006 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Methods for enantioselective transfer of carbenes starting from precursors carrying two carbonyl groups have been elaborated. A one-pot procedure for olefin cyclopropanation with CH-acidic precursors via intermediate phenyliodonium ylides has been developed. The structure of the [Rh₂{(S)-nttl}₄] catalyst was optimized to produce up to 98% ee in olefin cyclopropanations with dimethyl malonate or Meldrum’s acid. Highly selective Rh(II)-catalyzed olefin cyclopropanations could be observed upon replacement of methyl diazoacetoacetate by methyl (silyloxy-vinyl)diazoacetate. Enantioselective dipolar cycloadditions of diazopyruvate to polar olefins have been realized with Ru(II)-pybox catalysts.

Key words

carbenoids - catalysis - diazo decomposition - phenyliodonium ylides - rhodium

References

1a Pfaltz A. In Comprehensive Asymmetric Catalysis Jacobsen EN. Pfaltz A. Yamamoto H. Springer; Berlin: 1999. Vol. 3: p.513-538

Google Scholar
1b Doyle MP. In Catalytic Asymmetric Synthesis Ojima I. VCH; Weinheim: 1993.

Google Scholar
2 Doyle MP. McKervey MA. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds. From Cyclopropanes to Ylides Wiley; New York: 1998.

Google Scholar
3a Davies HML. Aldrichimica Acta 1997, 30: 107

Google Scholar
3b Davies HML. Antoulinakis EG. Org. React. 2001, 57: 1

Google Scholar
4 Davies HML. Panaro SA. Tetrahedron 2000, 56: 4871

Crossref Google Scholar
5 Doyle MP. Davies SB. Hu W. Org. Lett. 2000, 2: 1145

Google Scholar
6 Müller P. Acc. Chem. Res. 2004, 37: 243

Crossref Google Scholar
7 Müller P. Fruit C. Chem. Rev. 2003, 103: 2905

Crossref Google Scholar
8 Müller P. Allenbach Y. Robert E. Tetrahedron: Asymmetry 2003, 14: 779

Crossref Google Scholar
9a Dauban P. Dodd RH. Org. Lett. 2000, 2: 2327

Google Scholar
9b Espino CG. Du Bois J. Angew. Chem. Int. Ed. 2001, 40: 598

Google Scholar
10 Dauban P. Sanière T. Tarrade A. Dodd RH. J. Am. Chem. Soc. 2001, 123: 7707

Crossref PubMed Google Scholar
11a Wurz RP. Charette AB. Org. Lett. 2003, 5: 2327

Crossref PubMed Google Scholar
11b Wurz RP. Charette AB. J. Org. Chem. 2004, 69: 1262

Crossref PubMed Google Scholar
12a Müller P. Ghanem A. Synlett 2003, 1830

Crossref Google Scholar
12b Müller P. Ghanem A. Org. Lett. 2004, 6: 4347

Crossref Google Scholar
13 Davies HML. Ahmed G. Calvo RL. Churchill MR. Churchill DG. J. Org. Chem. 1998, 63: 2641

Crossref Google Scholar
14 Müller P. Allenbach Y. Ferri M. Bernardinelli GH. Flack HF. Org. Lett. 2004, 6: 1725

Crossref Google Scholar
15 Müller P. Allenbach YF. Grass S. Tetrahedron: Asymmetry 2005, 16: 2007

Crossref Google Scholar
16a Davies HML. Doan BD. J. Org. Chem. 1999, 64: 8501

Crossref Google Scholar
16b Davies HML. Doan BD. Tetrahedron Lett. 1996, 37: 3967

Crossref Google Scholar
17 Fok ME. Li C. Marino JP. Overman LE. J. Am. Chem. Soc. 1999, 121: 5467

Crossref Google Scholar
18 Müller P. Bernardinelli G. Allenbach YF. Ferri M. Grass S. Synlett 2005, 1397

Article in Thieme Connect Google Scholar
19 Alonso M.-E. Morales A. Chitty AW. J. Org. Chem. 1982, 47: 3747

Crossref Google Scholar
20a Pirrung MC. Zhang J. Lackey K. Sternbach DD. Brown F. J. Org. Chem. 1985, 60: 2112

Google Scholar
20b Pirrung MC. Zhang J. McPhail AT. J. Org. Chem. 1991, 56: 6269

Google Scholar
20c Pirrung MC. Lee YR. Tetrahedron Lett. 1994, 35: 6231

Google Scholar
20d Pirrung MC. Lee YR. J. Am. Chem. Soc. 1995, 117: 4814

Google Scholar
20e Pirrung MC. Blume F. J. Org. Chem. 1999, 64: 3642

Google Scholar
20f Pirrung MC. Kalliappan KP. Org. Lett. 2000, 3: 353

Google Scholar
21a Alonso M.-E. Jano P. Hernandez MI. Greenberg RS. Wenkert E. J. Org. Chem. 1983, 48: 3047

Crossref Google Scholar
21b Wenkert E. Alonso M.-E. Buckwalter EL. Sanchez EL. J. Am. Chem. Soc. 1983, 105: 2021

Crossref Google Scholar
21c Alonso M.-E. Hernandez MI. Gomez M. Jano P. Pekerar S. Tetrahedron 1985, 41: 2347

Crossref Google Scholar
22a Pirrung MC. Zhang J. Tetrahedron Lett. 1992, 33: 5987

Crossref Google Scholar
22b Ishitani H. Achiwa K. Heterocycles 1997, 46: 153

Crossref Google Scholar
23a Müller P. Allenbach YF. Bernardinelli G. Helv. Chim. Acta 2003, 86: 3164

Google Scholar
23b Müller P. Allenbach YF. Ferri M. Bernardinelli G. Arkivoc 2003, (vii): 80 ; www.arkat-usa.org

Google Scholar
24 Bachmann S. Mezzetti A. Helv. Chim. Acta 2001, 84: 3963

Google Scholar
25a Müller P. Chappellet S. Synlett 2004, 2573

Crossref Google Scholar
25b Müller P. Chappellet S. Helv. Chim. Acta 2005, 88: 1010

Crossref Google Scholar
26 Davies HLM. Bruzinski PR. Lake DH. Kong N. Fall MJ. J. Am. Chem. Soc. 1996, 118: 6897

Google Scholar
27 Roos GHP. McKervey AE. Synth. Commun. 1992, 22: 1751

Crossref Google Scholar
28 Hashimoto S.-I. Watanabe N. Ikegami S. Tetrahedron Lett. 1993, 34: 5173

Crossref Google Scholar
29 Watanabe N. Ogawa T. Ohtake Y. Ikegami S. Hashimoto S. Synlett 1996, 85

Article in Thieme Connect Google Scholar
30 Doyle MP. Winchester WN. Protopopova MN. Kazala AP. Westrum LJ. Org. Synth. 1995, 73: 13

Google Scholar
31 Nishiyama H. Itoh Y. Sugawara Y. Matsumoto K. Aoki K. Itoh K. Bull. Chem. Soc. Jpn. 1995, 68: 1253

Google Scholar