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The title compound, spiro[1-bromo-4-l-menthyloxy-5-oxo-6-oxa-bicyclo[3.1.0]-hexane-2,2-3-(16-methoxyacetatyl-4-l-menthyloxybutyrolactone)] 1, was obtained via tandem asymmetric double Michael addition/internal nucleophilic substitution of the chiral synthon, 5-l-menthyloxy-3-bromo-2-(5H)-furanone 2 with methoxy α-chloroacetate as a nucleophile under mild conditions, and structurally determined by single-crystal X-ray diffraction. Crystal data: C31H47BrO9, Mr = 643.60, orthorhombic, space group P212121, a = 9.6564(7), b = 14.8994(11), c = 23.6771(17) , V = 3406.5(4) 3, Z = 4, Dc = 1.255 g/cm3, λ(MoKα) = 0.71073 , μ = 1.254 mm-1 and F(000) = 1360. The structure was refined to R = 0.0324 and wR = 0.0737 for 5123 observed reflections (I > 2σ(I)). The crystallographic results of molecule 1 show that the interesting reaction of 2 with methoxy α-chloroacetate, in the usual manner, gave the spiro-cyclopropane skeleton with O-linked derivative containing multiple stereogenic centers 1 rather than the expected C-linked derivative.
The title compound, spiro [1-bromo-4-l-menthyloxy-5-oxo-6-oxa-bicyclo [3.1.0] -hexane-2,2-3- (16-methoxyacetat-4-l-menthyloxybutyrolactone) ] 1, was obtained via tandem asymmetric double Michael addition / internal nucleophilic substitution of the chiral synthon, 5-l-menthyloxy-3-bromo- 2- (5H) -furanone 2 with methoxy α-chloroacetate as a nucleophile under mild conditions, Crystal structure: C31H47BrO9, Mr = 643.60, orthorhombic, space group P212121, a = 9.6564 (7), b = 14.8994 (11), c = 23.6771 (17), V = 3406.5 (4) 3, Z = 4, Dc = 1.255 g / cm3, λ (MoKα) = 0.71073, μ = 1.254 mm -1 and F (000) = 1360. The structure was refined to R = 0.0324 and wR = for 5123 observed reflections (I> 2σ (I)). The crystallographic results of molecule 1 show that the interesting reaction of 2 with methoxy α-chloroacetate, in the usual manner, gave the spiro-cyclopropane skeleton with O-linked derivative multiple stereogenic centers 1 rat her than the expected C-linked derivative.