8,9-Isopropyl­idenedi­oxy-3-p-tolyl-1,6-dioxa-3-aza­spiro­[4.5]decane-2,10-dione

Chun-Sheng Ling; Qiang Wu; Shan-Shan Li

doi:10.1107/S1600536808034259

. 2008 Oct 25;64(Pt 11):o2181. doi: 10.1107/S1600536808034259

8,9-Isopropylidenedioxy-3-p-tolyl-1,6-dioxa-3-azaspiro[4.5]decane-2,10-dione

Chun-Sheng Ling ^a, Qiang Wu ^b,^*, Shan-Shan Li ^c

PMCID: PMC2959605 PMID: 21581040

Abstract

In the title compound, C₁₇H₁₉NO₆, which may serve as a ketone catalyst for the asymmetric epoxidation of olefins, the crystal packing is consolidated by C—H⋯O interactions.

Related literature

For general background, see: Denmark & Wu (1999 ▶); Shi (2004 ▶); Yang (2004 ▶). For the synthesis, see: Zhao et al. (2006 ▶). graphic file with name e-64-o2181-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₉NO₆
M _r = 333.33
Monoclinic,
a = 11.1268 (8) Å
b = 6.3163 (5) Å
c = 11.8697 (8) Å
β = 94.084 (1)°
V = 832.09 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 (2) K
0.18 × 0.15 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.982, T _max = 0.987
8821 measured reflections
1795 independent reflections
1389 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.075
S = 1.06
1795 reflections
220 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034259/hb2819sup1.cif

e-64-o2181-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034259/hb2819Isup2.hkl

e-64-o2181-Isup2.hkl^{(88.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O1ⁱ	0.97	2.54	3.093 (3)	116
C14—H14B⋯O4ⁱⁱ	0.97	2.55	3.426 (3)	151

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the Basic Research Foundation for Natural Science of Henan University.

supplementary crystallographic information

Comment

Dioxiranes generated in situ from chiral ketones are effective for the asymmetric epoxidation of olefins (Denmark & Wu, 1999; Shi, 2004; Yang, 2004). As part of our own studies in this area, we now report the synthesis and structure of the title compound, (I).

The compound (I) consists of a four-ring system, including a phenyl ring, a pyran ring, a dioxolane ring and an oxazolidine ring, and which displays a chair molecular framework (Fig. 1). In the structure of (I), the S(6) ring of O4/C10/C11/C12/C13/C14 is nonplanar, charactrtized by a O4–C10–C11–C12 torsion angle of 61.1 (2) °. The stereogenic centres C10, C12 and C13 were assigned R, S, and S configurations, respectively.

In the crystal, some short C—H···O interactions (Table 1) may help to establish the packing (Fig. 2).

Experimental

The title compound was made by the method of Zhao et al. (2006), starting from D-glucose and 4-methyl-benzenamine to yield colorless blocks of (I). The molecular formula, C₁₇H₁₉NO₆, was established by ESI-MS, m/z: 356(M+Na), 334(M+H), 232, 204, 108. Spectroscopic analysis, 1H NMR (400 MHz, CDCl₃): δ7.40 (d, J=5.4 Hz, 2H, ArH), 7.19 (d, J=5.4 Hz, 2H, ArH), 4.87 (d, J=5.7 Hz, 1H), 4.74 (d, J=10.2 Hz, 1H), 4.66–4.61 (m, 2H), 4.27 (d, J=13.8 Hz, 1H), 3.74 (d, J=10.2 Hz, 1H), 2.34 (s, 3H, ArCH₃), 1.49 (s, 3H, –CH₃), 1.44 (s, 3H, –CH₃).