Highly enantioselective synthesis of γ-substituted butenolides via the vinylogous Mukaiyama-Michael reaction catalyzed by a chiral scandium(iii)-N,N'-dioxide complex.
Zhang, Qi; Xiao, Xiao; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming; Organic & biomolecular chemistry 9 (2011) 5748–5754; doi:10.1039/c1ob05558e

data_7151952
_publ_section_title
;
 Highly enantioselective synthesis of \g-substituted butenolides via
 the vinylogous Mukaiyama-Michael reaction catalyzed by a chiral
 scandium(iii)-N,N'-dioxide complex.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5748
_journal_page_last               5754
_journal_paper_doi               10.1039/c1ob05558e
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H14 Cl2 O3'
_chemical_formula_sum            'C19 H14 Cl2 O3'
_chemical_formula_weight         361.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Tue Oct 12 11:22:44 2010'
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_audit_creation_method
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.887(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1115(3)
_cell_length_b                   5.6573(2)
_cell_length_c                   18.0697(7)
_cell_measurement_reflns_used    2610
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.0231
_cell_measurement_theta_min      3.2872
_cell_volume                     828.15(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
1 omega -78.00 -52.00 1.0000 4.5000
omega____ theta____ kappa____ phi______ frames
- -17.0486 131.0000 108.0000 26

2 omega -2.00 90.00 1.0000 4.5000
omega____ theta____ kappa____ phi______ frames
- 20.0174 38.0000 -60.0000 92

3 omega 6.00 91.00 1.0000 4.5000
omega____ theta____ kappa____ phi______ frames
- 20.0174 38.0000 -150.0000 85

4 omega -90.00 -55.00 1.0000 4.5000
omega____ theta____ kappa____ phi______ frames
- -17.0486 0.0000 -60.0000 35
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0820147000
_diffrn_orient_matrix_UB_12      0.0088002000
_diffrn_orient_matrix_UB_13      0.0115909000
_diffrn_orient_matrix_UB_21      -0.0300715000
_diffrn_orient_matrix_UB_22      -0.0006499000
_diffrn_orient_matrix_UB_23      -0.0375371000
_diffrn_orient_matrix_UB_31      -0.0056305000
_diffrn_orient_matrix_UB_32      -0.1251075000
_diffrn_orient_matrix_UB_33      0.0010187000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4126
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         29.0231
_diffrn_reflns_theta_min         3.2872
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0602
_reflns_number_gt                2484
_reflns_number_total             2764
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05558e.txt
_cod_data_source_block           20101012_s3_zq
_cod_original_cell_volume        828.15(6)
_cod_database_code               7151952
_chemical_oxdiff_formula         C50H40O8Cl6
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32