(2S)-2-(3-Oxo-1,4-dioxaspiro­[4.5]decan-2-yl)ethanoic acid

Tsai, Y.-F.; Su, Y.-T.; Lin, C.-H.

doi:10.1107/S160053680801146X

Volume 64
Part 5
Page o939
May 2008

Received 11 March 2008
Accepted 22 April 2008
Online 30 April 2008

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.124
Data-to-parameter ratio = 16.0
Details

(2S)-2-(3-Oxo-1,4-dioxaspiro[4.5]decan-2-yl)ethanoic acid

Yow-Fu Tsai,^a ^* Yu-Ting Su ^a and Chia-Her Lin ^a

^aDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li 320, Taiwan
Correspondence e-mail: tsaiyofu@cycu.edu.tw

The title compound, C₁₀H₁₄O₅, is an intermediate in our study of the asymmetric synthesis of [alpha] -hydroxyalkanoic acids. The structure consists of 1,4-dioxaspiro[4,5]decane skeleton formed when the cyclohexylidene group binds to both of the hydroxyl groups of carboxylic groups of the starting malic acid. The six-membered ring adopts a chair conformation.

Related literature

For related literature, see: Coppola & Schuster (1997); Díez et al. (2001); Dixon et al. (2005); Hanessian et al. (1993); Heimgartner & Obrecht (1990); Horgen et al. (2000); Liang et al. (2000); Sitachitta et al. (2000); Sugiyama et al. (1990).

Experimental

Crystal data

C₁₀H₁₄O₅
M_r = 214.21
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.7098 (6) Å
b = 10.3463 (8) Å
c = 15.3175 (13) Å
V = 1063.37 (15) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 295 (2) K
0.50 × 0.45 × 0.35 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scanSADABS; Bruker, 2004) T_min = 0.948, T_max = 0.963
7861 measured reflections
2206 independent reflections
1814 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.123
S = 1.05
2206 reflections
138 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.17 e Å^-3

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WK2081 ).

Acknowledgements

We gratefully acknowledge financial support in part from the National Science Council, Taiwan (NSC 96-2113-M-033-003) and in part from the project of the specific research fields in the Chung Yuan Christian University, Taiwan, under grant CYCU-95-CR-CH.

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Coppola, G. M. & Schuster, H. F. (1997). In [alpha] -Hydroxy Acids In Enantioselective Synthesis. Weinheim: Academic Press.
Díez, E., Dixon, D. J. & Ley, S. V. (2001). Angew. Chem. Int. Ed. 40, 2906-2909.
Dixon, D. J., Ley, S. V., Lohmann, S. & Sheppard, T. D. (2005). Synlett, 481-484.
Hanessian, S., Tehim, A. & Chen, P. (1993). J. Org. Chem. 58, 7768-7781.
Heimgartner, H. & Obrecht, D. (1990). Helv. Chim. Acta, 73, 221-228.
Horgen, F. D., Yoshida, W. Y. & Scheuer, P. J. (2000). J. Nat. Prod. 63, 461-467.
Liang, J., Moher, E. D., Moore, R. E. & Hoard, D. W. (2000). J. Org. Chem. 65, 3143-3147.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sitachitta, N., Williamson, R. T. & Gerwick, W. H. (2000). J. Nat. Prod. 63, 197-200.
Sugiyama, T., Murayama, T. & Yamashita, K. (1990). Tetrahedron Lett. 31, 7343-7344.

organic compounds