2018
DOI: 10.1002/anie.201805908
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Abstract: Reported herein is the first rhodium-catalyzed [4+2+1] cycloaddition of in situ generated ene/yne-ene-allenes and CO to synthesize challenging seven-membered carbocycles fused with five-membered rings. This reaction is designed based on the 1,3-acyloxy migration of ene/yne-ene-propargyl esters to ene/yne-ene-allenes, followed by oxidative cyclization, CO insertion, and reductive elimination to form the final [4+2+1] cycloadducts. The possible competing [4+1], [4+2], and [2+2+1] cycloadditions were disfavored, … Show more

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Cited by 21 publications
(15 citation statements)
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“…Recently, we achieved the first synthesis of a seven‐membered ring by using in situ‐generated vinylallenes in the [4+2+1] reaction of ene/yne‐ene‐propargyl esters and CO, where vinylallenes, alkenes/alkynes, and CO act as C 4 , C 2 , and C 1 synthons, respectively (Scheme 1 b). [1q] In this [4+2+1] reaction, the vinylallene intermediates were generated by the 1,3‐acyloxy migration of propargyl esters (Scheme 1 b). [3,8] Encouraged by this success, we further envisioned that the allene and alkene moieties of vinylallenes could switch their positions in the substrates.…”
Section: Methodsmentioning
confidence: 99%
“…Recently, we achieved the first synthesis of a seven‐membered ring by using in situ‐generated vinylallenes in the [4+2+1] reaction of ene/yne‐ene‐propargyl esters and CO, where vinylallenes, alkenes/alkynes, and CO act as C 4 , C 2 , and C 1 synthons, respectively (Scheme 1 b). [1q] In this [4+2+1] reaction, the vinylallene intermediates were generated by the 1,3‐acyloxy migration of propargyl esters (Scheme 1 b). [3,8] Encouraged by this success, we further envisioned that the allene and alkene moieties of vinylallenes could switch their positions in the substrates.…”
Section: Methodsmentioning
confidence: 99%
“…In 2018, Yu and co-workersr eported rhodium-catalyzed [4+ +2+ +1] cycloadditionso fi ns itu generatede ne/yne-ene-allenes 71 and CO to synthesize challenging [5,7]-fused carbocycles 70 (Scheme18). [24] This reaction features easily prepared substrates and broad reactions cope. This reaction is designed based on the 1,3-acyloxy migration of ene/yne-ene-propargyl esters 69 to ene/yne-ene-allenes 71,f ollowed by oxidative cyclization, CO insertion, and reductive elimination to form the final [4+ +2+ +1] cycloadducts.…”
Section: Transition-metal-catalyzed[ 4 + +2+ +1] Cycloaddition Reactionmentioning
confidence: 99%
“…3 Cycloadditions using allenes generated in situ from readily available propargyl esters via transition-metal-catalyzed 1,3-acyloxy migration have also been explored as a means to produce various polycyclic molecules. 4 In 2005, Zhang reported the gold-catalyzed 1,3-acyloxy migration of propargyl esters, followed by [2 + 2] cycloaddition, to produce cyclobutane-fused indolines (Scheme 1A). 5 Many variants of this pioneering study have since been reported, including [2 + 2], 6 [3 + 2], 7 [4 + 1], 8 [4 + 2], 9 [5 + 1], 10 and [4 + 2 + 1] 11 cycloadditions.…”
mentioning
confidence: 99%