FeCl₃-Promoted One-Step Synthesis of Spiro[4.5]decane Derivatives

Abstract

A FeCl₃-promoted synthesis of spiro[4.5]decane derivatives has been developed from 2-(5,5-dimethoxypentyl)-1-substituted cyclopentanols with high diastereoselectivity. These interesting compounds are formed through a cascade process involving a FeCl₃-promoted dehydration of alcohol followed by FeCl₃-mediated Prins cyclization.

Key words

spiro[4.5]decane - FeCl₃ - Prins cyclization - α-hydroxy alkynyl acetals - diastereoselectivity

References and Notes

• 1 Prins HJ. Chem. Weekbl.  1919,  16:  1072 
• 2 Pastor IM. Yus M. Curr. Org. Chem.  2007,  11:  925 
• 3 Ishihara K. Nakamura H. Yamamoto H. Synlett  2000,  1245 
• 4a Hopkins MH. Overman LE. Rishton GM. J. Am. Chem. Soc.  1991,  113:  5354 
• 4b Brown MJ. Harrison T. Herrinton PM. Hopkins MH. Hutchinson KD. Mishra P. Overman LE. J. Am. Chem. Soc.  1991,  113:  5365 
• 4c Trost BM. Chen DWC. J. Am. Chem. Soc.  1996,  118:  12541 
• 4d Minor KP. Overman LE. Tetrahedron  1997,  53:  8927 
• 4e Hanaki N. Link JT. MacMillan DWC. Overman LE. Trankle WG. Wurster JA. Org. Lett.  2000,  2:  223 
• 4f Cohen F. MacMillan DWC. Overman LE. Romero A. Org. Lett.  2001,  3:  1225 
• 4g Gahman TC. Overman LE. Tetrahedron  2002,  58:  6473 
• 4h Overman LE. Wolfe JP. J. Org. Chem.  2002,  67:  6421 
• 4i Burke BJ. Lebsack AD. Overman LE. Synlett  2004,  1387 
• 5 Kopecky DJ. Rychnovsky SD. J. Am. Chem. Soc.  2001,  123:  8420 
• 6a Overman LE. Castañeda A. Blumenkopf TA. J. Am. Chem. Soc.  1986,  108:  1303 
• 6b Kiyooka S.-I. Shiomi Y. Kira H. Kaneko Y. Tanimori S. J. Org. Chem.  1994,  59:  1958 
• 6c Chen C. Mariano PS. J. Org. Chem.  2000,  65:  3252 
• 6d Shin C. Chavre SN. Pae AN. Cha JH. Koh HY. Chang MH. Choi JH. Cho YS. Org. Lett.  2005,  7:  3283 
• 7 Kim Y.-H. Lee K.-Y. Oh C.-Y. Yang J.-G. Ham W.-H. Tetrahedron Lett.  2002,  43:  837 
• 10a Keinan E. Mazur Y. J. Org. Chem.  1978,  43:  1020 
• 10b Fadel A. Salaün J. Tetrahedron  1985,  41:  413 
• 10c Díaz DD. Miranda PO. Padrón JI. Martín VS. Curr. Org. Chem.  2006,  10:  457 
• 11 Jaber JJ. Mitsui K. Rychnovsky SD. J. Org. Chem.  2001,  66:  4679 

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The preparation of 1a is described in the Supporting Information.

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CCDC-781108 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/deposit [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax [phone]; email: [e-mail]].