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8306343 
Journal Article 
Synthesis and crystal structure of spiro[1-bromo-4-l-menthyloxy-5-oxo-6- oxa-bicyclo[3.1.0]hexane-2,2′-3′-(16″-methoxyacetatyl- 4′-l-menthyloxybutyrolactone)] 
Guo, JB; Wang, JG; Shi, QS; Chen, QH 
2007 
Yes 
Chinese Journal of Structural Chemistry
ISSN: 0254-5861 
26 
1 
49-54 
English 
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: C31H 47BrO9, Mr, = 643.60, orthorhombic, space group P212121, a = 9.6564(7), b = 14.8994(11), c = 23.6771(17) Å, V = 3406.5(4) Å3, Z = 4, Dc= 1.255 g/cm3, λ(MoKα) = 0.71073 Å, 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 > 2 σ(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. 
Asymmetric tandem reaction; Chiral spiro-cyclopropane skeleton with O-linked derivative; Optically active molecule; X-ray crystallography