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- W1978315522 abstract "Abstract Here we summarise our results for SmI 2 ‐induced 5‐ exo ‐ trig to 8‐ exo ‐ trig reductive cyclisations of suitably substituted indole and pyrrole derivatives. All precursors were easily prepared by simple N ‐alkylation or N ‐acylation of indole and pyrrole derivatives with the corresponding iodo alkanones, acid chlorides or lactones. The SmI 2 ‐induced cyclisations in most cases provided tri‐ and tetracyclic derivatives, even in the absence of HMPA, in good to very good yields and with excellent diastereoselectivities. Extensive investigations of the reaction conditions revealed that in the presence of different proton sources SmI 2 ‐induced cyclisations afforded mainly one major type of diastereomer (thermodynamic control), so the formation of three or four stereogenic centres is controlled in one step. The mechanism of the SmI 2 ‐induced ketyl coupling is discussed in more detail on the basis of these observations and two possible mechanistic pathways are compared. The assumed intermediate samarium enolates were also trapped with allyl iodide, furnishing interesting polycyclic N‐heterocycles bearing newly formed quaternary centres as single diastereomers." @default.
- W1978315522 created "2016-06-24" @default.
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- W1978315522 date "2010-04-27" @default.
- W1978315522 modified "2023-10-18" @default.
- W1978315522 title "Highly Diastereoselective Samarium Diiodide Induced Ketyl Cyclisations of Indole and Pyrrole Derivatives – Scope and Limitations" @default.
- W1978315522 cites W1544807337 @default.
- W1978315522 cites W1964799722 @default.
- W1978315522 cites W1966512781 @default.
- W1978315522 cites W1968479718 @default.
- W1978315522 cites W1969109708 @default.
- W1978315522 cites W1971986116 @default.
- W1978315522 cites W1972608757 @default.
- W1978315522 cites W1973006112 @default.
- W1978315522 cites W1976742711 @default.
- W1978315522 cites W1977515361 @default.
- W1978315522 cites W1978868477 @default.
- W1978315522 cites W1980829913 @default.
- W1978315522 cites W1982122229 @default.
- W1978315522 cites W1983537205 @default.
- W1978315522 cites W1986024013 @default.
- W1978315522 cites W1991684358 @default.
- W1978315522 cites W1994419025 @default.
- W1978315522 cites W1994423152 @default.
- W1978315522 cites W1999139342 @default.
- W1978315522 cites W2003951016 @default.
- W1978315522 cites W2013473498 @default.
- W1978315522 cites W2016853090 @default.
- W1978315522 cites W2017099548 @default.
- W1978315522 cites W2019588028 @default.
- W1978315522 cites W2020145463 @default.
- W1978315522 cites W2034860545 @default.
- W1978315522 cites W2038812261 @default.
- W1978315522 cites W2043261418 @default.
- W1978315522 cites W2043407516 @default.
- W1978315522 cites W2045783720 @default.
- W1978315522 cites W2050209156 @default.
- W1978315522 cites W2054036488 @default.
- W1978315522 cites W2055340564 @default.
- W1978315522 cites W2056014626 @default.
- W1978315522 cites W2058073539 @default.
- W1978315522 cites W2059020082 @default.
- W1978315522 cites W2059042954 @default.
- W1978315522 cites W2060227590 @default.
- W1978315522 cites W2061652513 @default.
- W1978315522 cites W2066281099 @default.
- W1978315522 cites W2071181513 @default.
- W1978315522 cites W2077759327 @default.
- W1978315522 cites W2084444657 @default.
- W1978315522 cites W2085485951 @default.
- W1978315522 cites W2089190019 @default.
- W1978315522 cites W2096892400 @default.
- W1978315522 cites W2104708001 @default.
- W1978315522 cites W2109074602 @default.
- W1978315522 cites W2109574402 @default.
- W1978315522 cites W2116919923 @default.
- W1978315522 cites W2120705954 @default.
- W1978315522 cites W2122092321 @default.
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- W1978315522 cites W2122253330 @default.
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- W1978315522 cites W2145807470 @default.
- W1978315522 cites W2155106053 @default.
- W1978315522 cites W2156607919 @default.
- W1978315522 cites W2159242371 @default.
- W1978315522 cites W2166071229 @default.
- W1978315522 cites W2170332690 @default.
- W1978315522 cites W2171082424 @default.
- W1978315522 cites W2179162529 @default.
- W1978315522 cites W2949068519 @default.
- W1978315522 cites W2949122995 @default.
- W1978315522 cites W2949250652 @default.
- W1978315522 cites W2949845068 @default.
- W1978315522 cites W2949854336 @default.
- W1978315522 cites W2950054709 @default.
- W1978315522 cites W2950259686 @default.
- W1978315522 cites W2950274334 @default.
- W1978315522 cites W2950927285 @default.
- W1978315522 cites W2951133342 @default.
- W1978315522 cites W2951781342 @default.
- W1978315522 cites W2952438363 @default.
- W1978315522 cites W2952639395 @default.
- W1978315522 cites W2952891513 @default.
- W1978315522 cites W2953050453 @default.
- W1978315522 cites W4231249836 @default.
- W1978315522 cites W4242134234 @default.
- W1978315522 cites W612383473 @default.
- W1978315522 doi "https://doi.org/10.1002/ejoc.200901455" @default.
- W1978315522 hasPublicationYear "2010" @default.
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