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

Börding, S.; Strohmann, C.; Preut, H.; Hiersemann, M.

doi:10.1107/S1600536811053840

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 (C-C) = 0.003 Å
R = 0.039
wR = 0.047
Data-to-parameter ratio = 15.2
Details

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

Sandra Börding,^a Carsten Strohmann,^a Hans Preut ^a ^* and Martin Hiersemann ^a

^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); Jang et al. (2011); Rezanka et al. (2004). For Evans alkylation, see: Evans et al. (1981, 1982).

Experimental

Crystal data

C₁₉H₂₄ClNO₅
M_r = 381.84
Monoclinic, P 2₁
a = 11.7552 (9) Å
b = 5.9139 (4) Å
c = 13.8789 (11) Å
= 109.023 (9)°
V = 912.16 (12) Å³
Z = 2
Mo K radiation
= 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 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.910, T_max = 0.954
6562 measured reflections
3594 independent reflections
2515 reflections with I > 2s(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.047
S = 0.98
3594 reflections
237 parameters
1 restraint
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.21 e Å^-3
Absolute structure: Flack (1983), 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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008) and PLATON (Spek, 2009); 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.
Evans, D. A., Ennis, M. D. & Marthre, D. J. (1982). J. Am. Chem. Soc. 104, 1737-1739.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gille, A. & Hiersemann, M. (2010). Org. Lett. 12, 5258-5261.
Jang, K. P., Choi, S. Y., Chung, Y. K. & Lee, E. (2011). Org. Lett. 13, 2476-2479.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds