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

Cheng-Hang Liu; Zhi-Xiang Yu

doi:10.1055/s-0037-1609199

Synlett, Table of Contents

Synlett 2018; 29(06): 764-768
DOI: 10.1055/s-0037-1609199

cluster

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

Cheng-Hang Liu

Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China Email: yuzx@pku.edu.cn

,

Zhi-Xiang Yu*

Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China Email: yuzx@pku.edu.cn

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Abstract

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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

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References

References and Notes

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13 CCDC 1562354 (2a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
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.
15 A rationalization of [3+2] and [5+2] cycloadditions has been given in our previous publication, see Ref. 8a.

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