Syn- and Anti-Selective Prins Cyclizations of δ,ε-Unsaturated Ketones to 1,3-Halohydrins with Lewis Acids
Ten acyclic and monocyclic δ,ε-unsaturated ketones, with and without methyl substituents on the double bond, underwent halide-terminated Prins (halo-Prins) cyclizations under anhydrous conditions in the presence of Lewis acids. TiCl4, TiBr4, BCl3, and BBr3 promoted syn-selective cyclizations to ster...
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Published in | Journal of organic chemistry Vol. 71; no. 4; pp. 1493 - 1501 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
17.02.2006
Amer Chemical Soc |
Subjects | |
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Abstract | Ten acyclic and monocyclic δ,ε-unsaturated ketones, with and without methyl substituents on the double bond, underwent halide-terminated Prins (halo-Prins) cyclizations under anhydrous conditions in the presence of Lewis acids. TiCl4, TiBr4, BCl3, and BBr3 promoted syn-selective cyclizations to sterically congested chloro- and bromohydrins, while SnCl4, SnBr4, InCl3, ZrCl4, and several other Lewis acids effected highly anti-selective reactions to furnish the corresponding trans halohydrins. The stronger Lewis acids (TiX4 and BX3) favor the syn process that involves axial delivery of a halide ligand. Competition experiments showed that substitution at the δ carbon (methallyl enones) led to increased rates (40−50-fold), while substitution at the ε position (cis and trans crotyl enones) retarded the rate and eroded the selectivity of the cyclizations. The trends in syn vs anti selectivity, reactivity, and effects of different Lewis acidic metal halides are rationalized by competitive reaction pathways proceeding through syn carbocation−halide ion pairs and a higher order transition state that leads to inversion of configuration and formation of trans halohydrins, along with cyclic olefins arising from proton elimination. |
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AbstractList | Ten acyclic and monocyclic delta,epsilon-unsaturated ketones, with and without methyl substituents on the double bond, underwent halide-terminated Prins (halo-Prins) cyclizations under anhydrous conditions in the presence of Lewis acids. TiCl4, TiBr4, BCl3, and BBr3 promoted syn-selective cyclizations to sterically congested chloro- and bromohydrins, while SnCl4, SnBr4, InCl3, ZrCl4, and several other Lewis acids effected highly anti-selective reactions to furnish the corresponding trans halohydrins. The stronger Lewis acids (TiX4 and BX3) favor the syn process that involves axial delivery of a halide ligand. Competition experiments showed that substitution at the delta carbon (methallyl enones) led to increased rates (40-50-fold), while substitution at the epsilon position (cis and trans crotyl enones) retarded the rate and eroded the selectivity of the cyclizations. The trends in syn vs anti selectivity, reactivity, and effects of different Lewis acidic metal halides are rationalized by competitive reaction pathways proceeding through syn carbocation-halide ion pairs and a higher order transition state that leads to inversion of configuration and formation of trans halohydrins, along with cyclic olefins arising from proton elimination. Ten acyclic and monocyclic δ,ε-unsaturated ketones, with and without methyl substituents on the double bond, underwent halide-terminated Prins (halo-Prins) cyclizations under anhydrous conditions in the presence of Lewis acids. TiCl4, TiBr4, BCl3, and BBr3 promoted syn-selective cyclizations to sterically congested chloro- and bromohydrins, while SnCl4, SnBr4, InCl3, ZrCl4, and several other Lewis acids effected highly anti-selective reactions to furnish the corresponding trans halohydrins. The stronger Lewis acids (TiX4 and BX3) favor the syn process that involves axial delivery of a halide ligand. Competition experiments showed that substitution at the δ carbon (methallyl enones) led to increased rates (40−50-fold), while substitution at the ε position (cis and trans crotyl enones) retarded the rate and eroded the selectivity of the cyclizations. The trends in syn vs anti selectivity, reactivity, and effects of different Lewis acidic metal halides are rationalized by competitive reaction pathways proceeding through syn carbocation−halide ion pairs and a higher order transition state that leads to inversion of configuration and formation of trans halohydrins, along with cyclic olefins arising from proton elimination. |
Author | Coates, Robert M Miles, R. Brandon Davis, Chad E |
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Keywords | EPOXIDES KETONES ALDEHYDE DIASTEREOSELECTIVE SYNTHESIS PI-CYCLIZATIONS STEREOCHEMISTRY ALPHA COPE REARRANGEMENT |
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Snippet | Ten acyclic and monocyclic δ,ε-unsaturated ketones, with and without methyl substituents on the double bond, underwent halide-terminated Prins (halo-Prins)... Ten acyclic and monocyclic delta,epsilon-unsaturated ketones, with and without methyl substituents on the double bond, underwent halide-terminated Prins... |
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StartPage | 1493 |
SubjectTerms | Acids Alcohols - chemical synthesis Chemistry Chemistry, Organic Chlorohydrins - chemical synthesis Cyclization Cycloparaffins Ketones - chemistry Physical Sciences Science & Technology Stereoisomerism |
Title | Syn- and Anti-Selective Prins Cyclizations of δ,ε-Unsaturated Ketones to 1,3-Halohydrins with Lewis Acids |
URI | http://dx.doi.org/10.1021/jo052142n https://api.istex.fr/ark:/67375/TPS-QJMK2FP5-T/fulltext.pdf http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000235453900025 https://www.ncbi.nlm.nih.gov/pubmed/16468798 https://search.proquest.com/docview/67651385 |
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