Matches in SemOpenAlex for { <https://semopenalex.org/work/W2070392004> ?p ?o ?g. }
- W2070392004 endingPage "1902" @default.
- W2070392004 startingPage "1895" @default.
- W2070392004 abstract "An intramolecular Simmons−Smith (IMSS) cyclopropanation has been developed, providing a novel method for the construction of substituted bicycloalkanes. First, functionalized gem-diiodoalkanes containing allylic alcohols were prepared in high yield. Then the intramolecular cyclization to form different ring sizes was investigated and proved to be successful for the synthesis of bicyclo[3.1.0]hexanes and bicyclo[4.1.0]heptanes. Larger chain lengths led to terminal alkene-containing products. Analysis of the product distribution for the different ring sizes and under various reaction conditions provided insight into the reactivity of substituted zinc carbenoids, and by the appropriate choice of conditions cyclopropanation could be promoted over alternative reaction pathways. Next the ability of allylic groups to promote the IMSS reaction by directing the zinc carbenoid was examined for the formation of bicycloheptanes. A scale of ‘directing-ability’ for these allylic groups has been rationalized, with an OMOM directing group providing the greatest enhancement in formation of the bicycle. Finally, the scope of the cyclization in forming substituted bicyclo[3.1.0]hexanes was explored. Substitution on the alkene and at the allylic position was well tolerated, providing the bicyclic products in high yields. Additionally, the IMSS reaction allowed a highly diastereoselective synthesis of a 5−3−5 fused tricycloalkane. These studies will have implications for the use of substituted carbenoids in cyclopropanation reactions and for directed cyclopropanation reactions as well as in the synthesis of substituted bicycloalkanes." @default.
- W2070392004 created "2016-06-24" @default.
- W2070392004 creator A5026261263 @default.
- W2070392004 creator A5035104027 @default.
- W2070392004 date "2010-01-21" @default.
- W2070392004 modified "2023-10-17" @default.
- W2070392004 title "Intramolecular Simmons−Smith Cyclopropanation. Studies into the Reactivity of Alkyl-Substituted Zinc Carbenoids, Effect of Directing Groups and Synthesis of Bicyclo[<i>n</i>.1.0]alkanes" @default.
- W2070392004 cites W1484990760 @default.
- W2070392004 cites W1964284609 @default.
- W2070392004 cites W1966927050 @default.
- W2070392004 cites W1967977239 @default.
- W2070392004 cites W1970803334 @default.
- W2070392004 cites W1975613503 @default.
- W2070392004 cites W1977732935 @default.
- W2070392004 cites W1980368805 @default.
- W2070392004 cites W1981059174 @default.
- W2070392004 cites W1981080459 @default.
- W2070392004 cites W1984764417 @default.
- W2070392004 cites W1985524348 @default.
- W2070392004 cites W1987438036 @default.
- W2070392004 cites W1989035218 @default.
- W2070392004 cites W1989516576 @default.
- W2070392004 cites W1994663228 @default.
- W2070392004 cites W1996212690 @default.
- W2070392004 cites W1996861242 @default.
- W2070392004 cites W1999664478 @default.
- W2070392004 cites W2001718158 @default.
- W2070392004 cites W2001767121 @default.
- W2070392004 cites W2003671277 @default.
- W2070392004 cites W2007847858 @default.
- W2070392004 cites W2009253289 @default.
- W2070392004 cites W2009747375 @default.
- W2070392004 cites W2015904106 @default.
- W2070392004 cites W2016991219 @default.
- W2070392004 cites W2018083767 @default.
- W2070392004 cites W2023714554 @default.
- W2070392004 cites W2027137290 @default.
- W2070392004 cites W2030717665 @default.
- W2070392004 cites W2030736591 @default.
- W2070392004 cites W2031521980 @default.
- W2070392004 cites W2036702039 @default.
- W2070392004 cites W2040841650 @default.
- W2070392004 cites W2041667674 @default.
- W2070392004 cites W2042452276 @default.
- W2070392004 cites W2044856625 @default.
- W2070392004 cites W2045329152 @default.
- W2070392004 cites W2045594965 @default.
- W2070392004 cites W2046418441 @default.
- W2070392004 cites W2048072572 @default.
- W2070392004 cites W2048748391 @default.
- W2070392004 cites W2050250997 @default.
- W2070392004 cites W2050597476 @default.
- W2070392004 cites W2050626326 @default.
- W2070392004 cites W2054047850 @default.
- W2070392004 cites W2057875354 @default.
- W2070392004 cites W2058045100 @default.
- W2070392004 cites W2058694265 @default.
- W2070392004 cites W2059666701 @default.
- W2070392004 cites W2059871580 @default.
- W2070392004 cites W2069130362 @default.
- W2070392004 cites W2070658650 @default.
- W2070392004 cites W2074960707 @default.
- W2070392004 cites W2078984998 @default.
- W2070392004 cites W2079630647 @default.
- W2070392004 cites W2080170386 @default.
- W2070392004 cites W2080662251 @default.
- W2070392004 cites W2081511316 @default.
- W2070392004 cites W2082838697 @default.
- W2070392004 cites W2084490387 @default.
- W2070392004 cites W2089582836 @default.
- W2070392004 cites W2098102595 @default.
- W2070392004 cites W2100323674 @default.
- W2070392004 cites W2100449760 @default.
- W2070392004 cites W2104591560 @default.
- W2070392004 cites W2107931809 @default.
- W2070392004 cites W2132325513 @default.
- W2070392004 cites W2142977237 @default.
- W2070392004 cites W2144321108 @default.
- W2070392004 cites W2147767064 @default.
- W2070392004 cites W2148437554 @default.
- W2070392004 cites W2159708877 @default.
- W2070392004 cites W2165382041 @default.
- W2070392004 cites W2165692144 @default.
- W2070392004 cites W2170141192 @default.
- W2070392004 cites W2178000870 @default.
- W2070392004 cites W2318324801 @default.
- W2070392004 cites W2328378929 @default.
- W2070392004 cites W2332275577 @default.
- W2070392004 cites W2356171203 @default.
- W2070392004 cites W2949079284 @default.
- W2070392004 cites W2949363620 @default.
- W2070392004 cites W2949566627 @default.
- W2070392004 cites W2949708628 @default.
- W2070392004 cites W2949761939 @default.
- W2070392004 cites W2950095003 @default.
- W2070392004 cites W2950400192 @default.
- W2070392004 cites W2950797181 @default.
- W2070392004 cites W2950996464 @default.