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Volume 68 
Part 1 
Page o169  
January 2012  

Received 28 November 2011
Accepted 14 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.047
Data-to-parameter ratio = 15.2
Details
Open access

(4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butanoyl}-1,3-oxazolidin-2-one

aFakultät Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany
Correspondence e-mail: hans.preut@tu-dortmund.de

The title compound, C19H24ClNO5, was synthesized and subsequently employed in an Evans alkylation. The purpose was to prove the absolute configuration in the projected synthesis of the side chain of (-)-Lytophilippine A. The oxazolidinone and the isopropylidene acetal rings have twisted conformations. The oxazolidinone and side-chain carbonyl groups are orientated in an antiperiplanar arrangement to minimize van der Waals repulsions. Furthermore, the Cl atom and the acetonide-protected secondary alcohol are also in an antiperiplanar arrangement with a torsion angle of 173.64 (14)°. The absolute configuration was determined and agrees with the configuration of the used chiral auxiliary.

Related literature

For background to the synthesis, see: Gille & Hiersemann (2010[Gille, A. & Hiersemann, M. (2010). Org. Lett. 12, 5258-5261.]); Jang et al. (2011[Jang, K. P., Choi, S. Y., Chung, Y. K. & Lee, E. (2011). Org. Lett. 13, 2476-2479.]); Rezanka et al. (2004[Rezanka, T., Hanus, L. O. & Dembitsky, V. M. (2004). Tetrahedron, 60, 12191-12199.]). For Evans alkylation, see: Evans et al. (1981[Evans, D. A., Bartroli, J. & Shih, T. L. (1981). J. Am. Chem. Soc. 103, 2127-2129.], 1982[Evans, D. A., Ennis, M. D. & Marthre, D. J. (1982). J. Am. Chem. Soc. 104, 1737-1739.]).

[Scheme 1]

Experimental

Crystal data
  • C19H24ClNO5

  • Mr = 381.84

  • Monoclinic, P 21

  • a = 11.7552 (9) Å

  • b = 5.9139 (4) Å

  • c = 13.8789 (11) Å

  • [beta] = 109.023 (9)°

  • V = 912.16 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 173 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.910, Tmax = 0.954

  • 6562 measured reflections

  • 3594 independent reflections

  • 2515 reflections with I > 2s(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.047

  • S = 0.98

  • 3594 reflections

  • 237 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1198 Friedel pairs

  • Flack parameter: 0.11 (5)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL-Plus.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2045 ).


References

Evans, D. A., Bartroli, J. & Shih, T. L. (1981). J. Am. Chem. Soc. 103, 2127-2129.  [CrossRef] [ChemPort] [ISI]
Evans, D. A., Ennis, M. D. & Marthre, D. J. (1982). J. Am. Chem. Soc. 104, 1737-1739.  [CrossRef] [ChemPort] [ISI]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gille, A. & Hiersemann, M. (2010). Org. Lett. 12, 5258-5261.  [ISI] [CrossRef] [ChemPort] [PubMed]
Jang, K. P., Choi, S. Y., Chung, Y. K. & Lee, E. (2011). Org. Lett. 13, 2476-2479.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Rezanka, T., Hanus, L. O. & Dembitsky, V. M. (2004). Tetrahedron, 60, 12191-12199.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o169  [ doi:10.1107/S1600536811053840 ]

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