Rh(I)-Catalyzed Intramolecular [3+2] Cycloaddition of trans-2-Allene-Vinylcyclopropanes

Published as part of the Cluster C–C Activation

Abstract

An intramolecular [3+2] cycloaddition of trans-2-allene-­vinylcyclopropanes for the synthesis of bicyclo[3.3.0]octane derivatives is developed.

Key words

allenes - vinylcyclopropanes - rhodium - [3+2] cycloaddition - bicyclo[3.3.0]octanes

• References and Notes


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[3+2] Cycloaddition of vinyl aziridines:
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• 14 Intramolecular [3+2] Cycloaddition; Typical ProcedureTo a mixture of Rh(CO)(PMe₃)₂Cl (3.2 mg, 0.01 mmol, 5 mol%) and AgOTf (2.6 mg, 0.01 mmol, 5 mol%) was added DCE (2 mL) and the mixture was stirred at room temperature under argon for 5 min. A solution of 1a (0.2 mmol) in DCE (2 mL) was added at room temperature, and the resulting solution was immersed into a preheated oil bath and stirred at 80 °C. After 20 h, the reaction mixture was cooled to room temperature and concentrated. The crude product was purified by flash column chromatography on silica gel to afford the [3+2] cycloadduct 2a. Run 1: 1a (67.5 mg) was converted into 2a (49.8 mg), yield 74%. Run 2: 1a (66.7 mg) was converted into 2a (48.1 mg), yield 72%. So, the average yield of two runs was 73%; white solid; mp 99–102 °C; R_f  = 0.59 (PE/EtOAc, 5:1); ¹H NMR (400 MHz, CDCl₃): δ = 7.70 (d, J = 8.2 Hz, 2 H), 7.33 (d, J = 8.2 Hz, 2 H), 5.65 (ddd, J = 17.0, 10.2, 6.3 Hz, 1 H), 4.90 (m, 1 H), 4.83 (m, 1 H), 3.53–3.43 (m, 1 H), 3.34–3.25 (m, 1 H), 3.24–3.14 (m, 2 H), 3.14–3.05 (m, 1 H), 2.95 (dd, J = 9.5, 7.3 Hz, 1 H), 2.71–2.58 (m, 1 H), 2.44 (s, 3 H), 1.69 (dd, J = 12.5, 6.9 Hz, 1 H), 1.62 (s, 3 H), 1.58 (s, 3 H), 1.56–1.48 (m, 1 H); ¹³C NMR (101 MHz, CDCl₃): δ = 143.3, 139.7 (+), 138.1, 133.2, 129.5 (+, 2 C), 127.6 (+, 2 C), 127.4, 112.9 (–), 52.8 (–), 52.2 (–), 47.1 (+), 45.8 (+), 41.7 (+), 36.8 (–), 22.0 (+), 21.5 (+), 21.0 (+), DEPT explanation in SI. HRMS (ESI): m/z [M + H]⁺ calcd for C₁₉H₂₆NO₂S: 332.1679; found: 332.1670.
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