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 2002(7): 0937-0940
DOI: 10.1055/s-2002-28501
DOI: 10.1055/s-2002-28501
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Indium(III) Complex-Catalyzed Tandem Carbonyl-Ene Reaction: An Efficient Construction of Tetrahydropyran Rings
Further Information
Received
1 March 2002
Publication Date:
14 May 2002 (online)
Publication History
Publication Date:
14 May 2002 (online)
Abstract
An atom economic and efficient construction of tetrahydropyran rings using Indium triflate-catalyzed self-tandem carbonyl-ene, intramolecular (2,5) oxonium-ene cyclization between aldehydes and methylene cyclohexane is reported.
Key words
indium(III) complex - tandem - carbonyl-ene - tetrahydropyran
- Some efforts towards the synthesis of natural products with tetrahydropyran units:
-
1a
Smith AB.Verhoest PR.Minbiole KP.Schelhaas M. J. Am. Chem. Soc. 2001, 123: 4834 -
1b
Smith AB.Safonov IG.Corbet RM. J. Am. Chem. Soc. 2001, 123: 12426 -
1c
Liu P.Jacobsen EN. J. Am. Chem. Soc. 2001, 123: 10772 -
1d
White JD.Kranemann CL.Kuntiyong P. Org. Lett. 2001, 3: 4003 -
1e
Evans DA.Cee VJ.Smith TE.Santiago KJ. Org. Lett. 1999, 1: 87 - For reviews, see:
-
2a
Mikami K.Shimizu M. Chem. Rev. 1992, 92: 1021 -
2b
Overman LE. Acc. Chem. Res. 1992, 25: 352 . For examples, see: -
2c
Blumenlopf TA.Look GC.Overman LE. J. Am. Chem. Soc. 1990, 112: 4399 -
2d
Ohmura H.Smyth GD.Mikami K. J. Org. Chem. 1999, 64: 6056 ; and references cited therein -
3a
Loh T.-P.Hu Q.-Y.Ma L.-T. J. Am. Chem. Soc. 2001, 123: 2450 -
3b
Loh T.-P.Tan K.-T.Hu Q.-Y. Angew. Chem., Int. Ed. Engl. 2001, 40: 2921 -
3c
Loh T.-P.Hu Q.-Y.Tan K.-T.Cheng H-S. Org. Lett. 2001, 3: 266 -
3d
Loh T-P.Hu Q.-Y.Chok Y.-K.Tan K.-T. Tetrahedron Lett. 2001, 42: 9277 - 4
Mikami K.Terada M.Nakai T. J. Am. Chem. Soc. 1990, 112: 3949