Direct Asymmetric Allylic Alkenylation of N-Itaconimides with Morita-Baylis-Hillman Carbonates
Wenguo Yang; Davin Tan; Lixin Li; Zhiqiang Han; Lin Yan; Kuo-Wei Huang; Choon-Hong Tan; Zhiyong Jiang; Journal of Organic Chemistry 77 (2012) 6600–6607; doi:10.1021/jo3012539

data_4027364
_publ_section_title
;
 Direct Asymmetric Allylic Alkenylation of N-Itaconimides with
 Morita-Baylis-Hillman Carbonates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6600
_journal_page_last               6607
_journal_paper_doi               10.1021/jo3012539
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H22 Br2 N2 O5'
_chemical_formula_sum            'C29 H22 Br2 N2 O5'
_chemical_formula_weight         638.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-03-29
_audit_creation_method
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.206(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.1512(11)
_cell_length_b                   10.2639(7)
_cell_length_c                   8.9612(4)
_cell_measurement_reflns_used    3565
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.0948
_cell_measurement_theta_min      4.5665
_cell_volume                     2665.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
1 omega -77.00 -52.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 0.0000 178.0000 -150.0000 25

2 omega -13.00 13.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 0.0000 57.0000 -180.0000 26

3 omega -111.00 -26.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -42.5000 -61.0000 150.0000 85

4 omega -48.00 27.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -42.5000 30.0000 30.0000 75

5 omega -118.00 -46.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -42.5000 178.0000 90.0000 72

6 omega -48.00 -16.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -42.5000 37.0000 -60.0000 32

7 omega -48.00 9.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -42.5000 37.0000 -30.0000 57

8 omega 4.00 29.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -42.5000 30.0000 60.0000 25

9 omega -112.00 -12.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -42.5000 -77.0000 -120.0000 100

10 omega 35.00 104.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 55.8596 57.0000 90.0000 69

11 omega 53.00 82.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -30.0000 -180.0000 29

12 omega 53.00 91.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -94.0000 -30.0000 38

13 omega 55.00 111.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -100.0000 -98.0000 56

14 omega 51.00 81.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -30.0000 30.0000 30

15 omega 130.00 164.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 61.0000 120.0000 34

16 omega 71.00 114.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -111.0000 150.0000 43

17 omega 87.00 178.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 30.0000 90.0000 91

18 omega 40.00 66.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -111.0000 150.0000 26

19 omega 41.00 94.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -45.0000 -90.0000 53

20 omega 52.00 94.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -94.0000 -180.0000 42

21 omega 42.00 71.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -45.0000 -180.0000 29

22 omega 63.00 94.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -45.0000 -150.0000 31

23 omega 39.00 164.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -15.0000 60.0000 125

24 omega 76.00 102.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -94.0000 0.0000 26

25 omega 45.00 98.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -45.0000 -30.0000 53

26 omega 57.00 145.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 178.0000 -180.0000 88

27 omega 51.00 131.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -61.0000 90.0000 80
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0376336000
_diffrn_orient_matrix_UB_12      -0.0970229000
_diffrn_orient_matrix_UB_13      0.0621695000
_diffrn_orient_matrix_UB_21      -0.0372331000
_diffrn_orient_matrix_UB_22      -0.1044302000
_diffrn_orient_matrix_UB_23      0.0147712000
_diffrn_orient_matrix_UB_31      0.0049925000
_diffrn_orient_matrix_UB_32      -0.0470010000
_diffrn_orient_matrix_UB_33      -0.1606362000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8441
_diffrn_reflns_theta_full        72.24
_diffrn_reflns_theta_max         72.24
_diffrn_reflns_theta_min         4.57
_diffrn_source                   'Enhance (Cu) x-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    4.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.034(16)
_refine_ls_extinction_coef       0.00256(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5103
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.5844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                4853
_reflns_number_total             5103
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3012539_si_001.cif
_cod_data_source_block           20120329
_cod_database_code               4027364
_chemical_oxdiff_formula         C20H20O4Br2
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97