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Synlett 2015; 26(11): 1553-1556
DOI: 10.1055/s-0034-1379926
DOI: 10.1055/s-0034-1379926
letter
Cycloaddition Reactions of Carbonyl Ylides Derived From Enones
Weitere Informationen
Publikationsverlauf
Received: 07. März 2015
Accepted after revision: 07. Mai 2015
Publikationsdatum:
03. Juni 2015 (online)
![](https://www.thieme-connect.de/media/synlett/201511/lookinside/thumbnails/st-2015-b0164-l_10-1055_s-0034-1379926-1.jpg)
To Prof. Peter Vollhardt on the occasion of his 69th birthday, and in appreciation of his contributions to Synlett
Abstract
The formation of unsaturated carbonyl ylides via rhodium-catalyzed carbene cyclization with enones and their subsequent inter- and intramolecular cycloadditions to construct functionalized oxapolycyclic rings have been realized.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379926.
- Supporting Information
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References and Notes
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- 12 Cycloaddition with electron-rich dipolarophiles such as 2-butyne, (Z)-1,4-diacetoxybut-2-ene, and ethoxyethene, also met with failure.
- 13 Experimental for the Reaction of Diazoketone 11 To a solution of Rh2(OAc)4 (25.2 mg, 0.0570 mmol) in dry CH2Cl2 (30 mL) was added predried 3 Å MS (0.48 g). After stirring for 10 min, diazoketoester 11 (61.2 mg, 0.220 mmol) in dry CH2Cl2 (10 mL) was added via cannula. The reaction was stirred at r.t. and monitored by TLC. When the reaction was complete (4 h), the mixture was filtered through a pad of Celite, and the plug was washed successively with several volumes of EtOAc. The filtrate was removed of volatiles in vacuo, and the residue was purified by flash chromatography using 5% EtOAc in hexane to afford 17 (39.6 mg, 72% yield) as a white solid. Rf = 0.15 (10% EtOAc in hexane). 1H NMR (600 MHz, C6D6): δ = 5.71–5.68 (m, 1 H), 5.63 (dd, J = 2.4, 10.0 Hz, 1 H), 4.16–4.03 (m, 2 H), 2.24–2.01 (m, 4 H), 1.82–1.77 (m, 1 H), 1.64 (d, J = 17.3 Hz, 1 H), 1.47–1.40 (m, 2 H), 1.36–1.30 (m, 3 H), 1.14–1.07 (m, 2 H), 0.99 (t, J = 7.2 Hz, 3 H) ppm. 13C NMR (150 MHz, C6D6): δ = 202.0, 168.0, 132.0, 128.9, 88.9, 79.6, 61.5, 40.5, 39.6, 38.3, 33.0, 29.3, 25.1, 14.2 ppm. IR (CH2Cl2): 3065, 2931, 1747, 1726, 1606, 1316, 1079, 947 cm–1. LRMS (EI): m/z (rel) = 250.1 (2) [M+], 92.1 (100), 91.1 (51), 93.1 (50), 117.1 (30), 134.1 (27), 106.1 (27), 79.0 (24). HRMS (EI): m/z calcd for C14H18O4 [M+]: 250.1205; found: 250.1195.
- 14 Full crystallographic data for 17 (CCDC 1051518) can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
Reviews on CCCC reactions: