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
Synthesis 2005(13): 2239-2245
DOI: 10.1055/s-2005-870000
DOI: 10.1055/s-2005-870000
PAPER
© Georg Thieme Verlag Stuttgart · New York
Diastereoselective Michael Additions of Chelated Enolates towards Nitroalkenes
Further Information
Received
25 February 2005
Publication Date:
13 July 2005 (online)
Publication History
Publication Date:
13 July 2005 (online)
![](https://www.thieme-connect.de/media/synthesis/200513/lookinside/thumbnails/10.1055-s-2005-870000-1.jpg)
Abstract
Highly reactive chelated enolates are versatile nucleophiles that underwent Michael additions towards nitroalkenes. The yields and selectivities obtained depend on the protecting groups and metal salts used. Zinc enolates in general give the best yields and the selectivities are high with tosylated glycinates. The best selectivities are obtained using tin enolates in combination with the TFA-protecting groups.
Key words
amino acids - chelated enolates - Michael additions - nitroalkenes
-
1a
Barrett AGM.Graboski GG. Chem. Rev. 1986, 86: 751 -
1b
Schäfer H.Seebach D. Tetrahedron 1995, 51: 2305 -
1c
Berner OM.Tedeschi L.Enders D. Eur. J. Org. Chem. 2002, 1869 -
2a
Seebach D.Colvin EW.Lehr F.Weller T. Chimia 1979, 33: 1 -
2b
Nitro Compounds - Recent Advances in Synthesis and Chemistry: Organic Nitro Chemistry Series
Feuer H.Nielsen AT. Wiley-VCH; Weinheim: 1990. -
2c
The Nitro Group in Organic Synthesis
Ono N. Wiley-VCH; New York: 2001. -
3a
Nef JUJ. Liebigs Ann. Chem. 1894, 280: 263 -
3b
Hassner A.Larkin JM.Dowd JE. J. Org. Chem. 1968, 33: 1733 -
3c
Pinnick HW. Org. React. (N.Y.) 1990, 38: 655 -
4a
Barton DHR.Fernandez I.Richard CS.Zard SZ. Tetrahedron 1987, 43: 551 -
4b
Albanese D.Landini D.Penso M. Synthesis 1990, 334 -
4c
Bartra M.Romea P.Urpi F.Vilarrasa J. Tetrahedron 1990, 46: 587 -
5a
Kornblum N.Fishbein L. J. Am. Chem. Soc. 1955, 77: 6266 -
5b
Beck AK.Seebach D. Chem. Ber. 1991, 124: 2897 -
6a
Jung ME.Long-Mei Z. Tetrahedron Lett. 1983, 24: 4533 -
6b
Saednya A. Synthesis 1983, 748 -
6c
Thomas HG.Greyn HD. Synthesis 1990, 129 -
7a
Mukaiyama T.Nambu H. J. Org. Chem. 1962, 27: 2201 -
7b
Wehrli PA.Schaer B. J. Org. Chem. 1977, 42: 3956 -
7c
Urpí F.Vilarrasa J. Tetrahedron Lett. 1990, 31: 7497 -
7d
Czekelius C.Carreira EM. Angew. Chem. Int Ed. 2005, 44: 612 ; Angew. Chem. 2005, 117, 618 - 8 Preliminary communication:
Mendler B.Kazmaier U. Org. Lett. 2005, 7: 1715 -
9a
Schöllkopf U.Kühnle W.Egert E.Dyrbusch M. Angew. Chem., Int. Ed. Engl. 1987, 26: 480 ; Angew. Chem. 1987, 99, 480 -
9b
Busch K.Groth UM.Kühnle W.Schöllkopf U. Tetrahedron 1992, 48: 5607 - 10
Brenner M.Seebach D. Helv. Chim. Acta 1999, 82: 2365 - Reviews:
-
11a
Kazmaier U. Liebigs Ann./Recl. 1997, 285 -
11b
Kazmaier U. In Bioorganic Chemistry Wiley-VCH; Weinheim: 1999. p.201-206 -
11c
Kazmaier U.Maier S.Zumpe FL. Synlett 2000, 1523 -
11d
Kazmaier U. In Claisen Rearrangements Wiley-VCH; Weinheim: 2005. p.in press -
12a
Kazmaier U.Zumpe FL. Angew. Chem. Int. Ed. 1999, 38: 1468 ; Angew. Chem. 1999, 111, 1572 -
12b
Kazmaier U.Zumpe FL. Angew. Chem. Int. Ed. 2000, 39: 802 ; Angew. Chem. 2000, 112, 805 -
12c
Kazmaier U.Pohlman M. Synlett 2004, 623 -
13a
Pohlman M.Kazmaier U. Org. Lett. 2003, 5: 2631 -
13b
Pohlman M.Kazmaier U.Lindner T. J. Org. Chem. 2004, 69: 6909