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
Synthesis 2002(2): 0191-0194
DOI: 10.1055/s-2002-19796
DOI: 10.1055/s-2002-19796
PAPER
© Georg Thieme Verlag Stuttgart · New York
A New General Route to Acceptor-Substituted Vinyloxiranes via Siloxyoxiranes - Novel Promising Synthetic Building-Blocks
Weitere Informationen
Received
16 August 2001
Publikationsdatum:
03. August 2004 (online)
Publikationsverlauf
Publikationsdatum:
03. August 2004 (online)
Abstract
Epoxidation of silyl enol ethers 2a,b with dimethyldioxirane yields siloxyoxiranes 3a,b. Anions 4a-d lead to nucleophilic ring-opening in the acetal position C-1 of 3 to give diols 5a-d. Monotosylation and cyclisation provide acceptor-substituted vinyloxiranes 6a-d.
Key words
dimethyldioxirane - silyl enol ethers - siloxyoxiranes - vinyloxiranes - epoxide ring opening
- 1
Gorzynski Smith J. Synthesis 1984, 629 - Recent examples:
-
2a
Gras JL. J. Org. Chem. 1981, 46: 3738 -
2b
Marino JP.de la Pradilla RF.Laborde E. J. Org. Chem. 1987, 52: 4898 -
2c
Narjes F.Schaumann E. Liebigs Ann. Chem. 1993, 841 -
2d
Trost BM.Lemoine RC. Tetrahedron Lett. 1996, 37: 9161 -
2e
Trost BM.Ceschi MA.König B. Angew. Chem., Int. Ed. Engl. 1997, 36: 1486 ; Angew. Chem. 1997, 109, 1562 -
2f
Fürstner A.Weintritt H. J. Am. Chem. Soc. 1998, 120: 2817 -
2g
Fürstner A.Gastner T.Rust J. Synlett 1999, 29 -
2h
Hertweck C.Boland W. J. Org. Chem. 1999, 64: 4426 -
2i
Baylon C.Prestat G.Heck M.-P.Mioskowski C. Tetrahedron Lett. 2000, 41: 3833 -
2j
Löfstedt J.Pettersson-Fasth H.Bäckvall J.-E. Tetrahedron 2000, 56: 2225 -
2k
Trost BM.Tang W.Schulte JL. Org. Lett. 2000, 2: 4013 -
3a For (2-bromovinyl)oxirane:
Beny J.-P.Pommelet J.-C.Chuche J. Bull Soc. Chim. Fr. 1981, 369 -
3b For (2-chlorovinyl)oxirane, e.g.:
Hawkins EGE. J. Chem. Soc. 1959, 248 -
3c
Bäckvall J.-E.Juntunen SK. J. Org. Chem. 1988, 53: 2398 -
3d
Bäckvall J.-E.Ericsson AM.Juntunen SK. J. Org. Chem. 1993, 58: 5221 - 4
Peterson PE.Nelson DJ.Risener R. J. Org. Chem. 1986, 51: 2381 -
5a
Rubottom GM.Vazquez MA.Pelegrina DR. Tetrahedron Lett. 1974, 4319 -
5b
Yamamoto H.Tsuda M.Sakaguchi S.Ishii Y. J. Org. Chem. 1997, 62: 7174 -
5c
Zhu Y.Tu Y.Yu H.Shil Y. Tetrahedron Lett. 1998, 39: 7819 -
5d
Adam W.Fell RT.Saha-Möller CR.Zhao C.-G. Tetrahedron: Asymmetry 1998, 9: 397 ; and references cited therein - 6
Davis FA.Sheppard AC. J. Org. Chem. 1987, 52: 954 - 7
Adam W.Bialas J.Hadjiarapoglou L. Chem. Ber. 1991, 124: 2377 - 8
Frormann S. Ph. D. Thesis Technische Universität Clausthal; Germany: 1994. - 9
Takeda T.Furukawa H.Fujimori M.Suzuki K.Fujiwara T. Bull. Chem. Soc. Jpn. 1984, 57: 1863 - 10
Chan TH.Ong BS. J. Org. Chem. 1978, 43: 2994 -
11a
Ottolenghi A.Fridkin M.Zilkha A. Can. J. Chem. 1963, 41: 2977 -
11b
Boeckman RK.Bruza KJ. Tetrahedron Lett. 1974, 3365 -
11c
Gröbel B.-T.Seebach D. Chem. Ber. 1977, 110: 867 - 12
Gao Y.Hanson RM.Klunder JM.Ko SY.Masamune H.Sharpless KB. J. Am. Chem. Soc. 1987, 109: 5765