Organic Letters
Letter
(13) For related dipoles, see: azlactones: (a) Melhado, A. D.; Luparia,
M.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12638. α-
Iminophosphonates: (b) Yamashita, Y.; Guo, X.-X.; Takashita, R.;
Kobayashi, S. J. Am. Chem. Soc. 2010, 132, 3262. α-Iminonitriles:
(c) Robles-Machín, R.; Alonso, I.; Adrio, J.; Carretero, J. C. Chem.
Eur. J. 2010, 16, 5286. (d) N-(2-Pyridylmethyl)imines: Padilla, S.;
Tejero, R.; Adrio, J.; Carretero, J. C. Org. Lett. 2010, 12, 5608. (e) α-
(programme AVANCAT; S2009/PPQ-1634) is greatly appre-
ciated. M.G.-E. and A.P.-E. thank the MINECO for predoctoral
contracts.
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(15) See the Supporting Information for details.
(16) Typical procedure for the Asymmetric [3 + 2] Cycloaddition:
(3aS,4S,6aR)-2-Phenyl-4-(2-pyridinyl)tetrahydropyrrolo[3,4-c]pyr-
role-1,3(2H,3aH)-dione (3a). To a solution of Walphos (15.8 mg,
17.10−3 mmol) and Cu(CH3CN)4PF6 (6.3 mg, 17.10−3 mmol) in
THF (0.5 mL), under nitrogen atmosphere, at −10 °C, were
successively added water (3 μL, 0.17 mmol), a solution of N-
phenylmaleimide (30.0 mg, 0.17 mmol) in THF (0.5 mL), and a
solution of 1a (50.0 mg, 0.26 mmol) in THF (0.5 mL). After 24 h at
−10 °C, the mixture was diluted with dichloromethane and washed
with ammonium hydroxide (3 × 5 mL) and brine (3 × 5 mL). The
organic layer was separated, dried over Na2SO4, and concentrated
under reduced pressure. The residue was purified by silica gel flash
chromatography (hexane−EtOAc 2:1) to afford a mixture (88:12) of
the cycloadduct trans-3a and cis-3a (43.9 mg, 87%, colorless solid).
(17) Crystallographic data of 3k are available in the Supporting
Information.
(18) In other 1,3-dipolar cycloadditions of (Z) sulfonyl acrylates, the
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