Cycloaddition Reactions of Carbonyl Ylides Derived From Enones

To Prof. Peter Vollhardt on the occasion of his 69^th 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.

Key words

carbenoids - ylides - cycloaddition - diazo compounds - domino reaction

• References and Notes

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• 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. R_f = 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.
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