π-Cyclizations of α-methoxycarbonyl oxycarbenium ions; synthesis of oxacyclic carboxylic esters
作者： Lucie D.M. Lolkema , Henk Hiemstra , Cindy Semeyn , W.Nico Speckamp
DOI: 10.1016/S0040-4020(01)85238-8
关键词: Intramolecular reaction 、 Double bond 、 Tetrahydropyran 、 Medicinal chemistry 、 Catalysis 、 Tin 、 Ion 、 Lewis acids and bases 、 Chemistry 、 Stereochemistry 、 Cationic polymerization
摘要: Abstract Acid-mediated cyclization reactions are described of seven methyl 2-acetoxy-2-(3-alken-1-oxy)acetates with different chain substitution. The major product the tin tetrachloride-induced reaction is in most cases a tetrahydropyran containing an equatorial carbomethoxy function at C2 and axial chlorine atom C4. mechanism its formation involves net cis -addition intermediate α-ester oxycarbenium ion to carbon-carbon double bond, likely caused by quasi orientation ester chair-like transition state. results interpreted invoking (1) occurrence 2-oxonia-Cope rearrangement (2) participation trapping cyclic cationic intermediate. cyclizations two 2-acetoxy-2-(4-alken-1-oxy)acetates 2-acetoxy-2-(alkynoxy)acetates also described.
narcis.nl
uva.nl
elsevier.com参考文章(60)
Larry E. Overman, Charge as a key component in reaction design. The invention of cationic cyclization reactions of importance in synthesis Accounts of Chemical Research. ,vol. 25, pp. 352- 359 ,(1992) , 10.1021/AR00020A005
Nikola A. Nikolic, Elizabeth Gonda, C. P. Desmond Longford, Nancy T. Lane, David W. Thompson, Preparation of cyclic ethers via a transacetalization-cationic cyclization sequence Journal of Organic Chemistry. ,vol. 54, pp. 2748- 2751 ,(1989) , 10.1021/JO00272A055
Laura Coppi, Alfredo Ricci, Maurizio Taddei, Synthesis of 4-halotetrahydropyrans from allylsilanes and carbonyl compounds in the presence of lewis acids Tetrahedron Letters. ,vol. 28, pp. 973- 976 ,(1987) , 10.1016/S0040-4039(00)95890-8
Armando Castaneda, David J. Kucera, Larry E. Overman, Preparation of seven-membered ring cyclic ethers and 3-alkylidenetetrahydropyrans from the cyclization of oxonium cations derived from unsubstituted and silicon-containing 4-alken-1-ols Journal of Organic Chemistry. ,vol. 54, pp. 5695- 5707 ,(1989) , 10.1021/JO00285A016
I.Trevor Kay, Emyr G. Williams, Spiroketals: The synthesis of an olive fly pheromone component, 4-hydroxy-1,7-dioxaspiro[5,5]undecane, via a novle cation-olefin cyclisation step Tetrahedron Letters. ,vol. 24, pp. 5915- 5918 ,(1983) , 10.1016/S0040-4039(00)94237-0
G. Stuart Cockerill, Philip Kocienski, Richard Treadgold, Silicon-mediated annulation. Part 2. A synthesis of β-alkoxy cyclo-octanones via intramolecular directed aldol reactions Journal of The Chemical Society-perkin Transactions 1. ,vol. 17, pp. 2101- 2108 ,(1985) , 10.1039/P19850002101
W.H. Bunnelle, D.W. Seamon, D.L. Mohler, T.F. Ball, D.W. Thompson, The synthesis of 4-halotetrahydropyrans and 4-halo-5,6-dihydro-2H-pyrans via the lewis acid promoted cyclization of acetals of homoallylic and homopropargylic alcohols Tetrahedron Letters. ,vol. 25, pp. 2653- 2654 ,(1984) , 10.1016/S0040-4039(01)81254-5
Z.Y Wei, J.S Li, D Wang, T.H Chan, Lewis acid promoted condensation of carbonyl compounds with alkoxyallylsilanes synthesis of substituted tetrahydropyrans Tetrahedron Letters. ,vol. 28, pp. 3441- 3444 ,(1987) , 10.1016/S0040-4039(00)96321-4
H.E. Schoemaker, J. Dijkink, W.N. Speckamp, Biomimetic α-acylimmonium cyclisations of unactivated olefin Tetrahedron. ,vol. 34, pp. 163- 172 ,(1978) , 10.1016/S0040-4020(01)93599-9
Hendrik H. Mooiweer, Kirsten W.A. Ettema, Henk Hiemstra, W. Nico Speckamp, Preparation of γ oxo-α-amino acids from silyl enol ethers and glycine cation equivalents; a facile synthesis of (±)-5-hydroxy.4.Oxonorvaline (HON) Tetrahedron. ,vol. 46, pp. 2991- 2998 ,(1990) , 10.1016/S0040-4020(01)88390-3