Enantio- and Diastereoselective Organocatalytic α-Alkylation of Aldehydes with 3-Substituted 2-(Bromomethyl)acrylates
Jacqueline Jiménez; Aitor Landa; Aitziber Lizarraga; Miguel Maestro; Antonia Mielgo; Mikel Oiarbide; Irene Velilla; Claudio Palomo; Journal of Organic Chemistry 77 (2012) 747–753; doi:10.1021/jo202073n

data_4026862
_publ_section_title
;
 Enantio- and Diastereoselective Organocatalytic \a-Alkylation of
 Aldehydes with 3-Substituted 2-(Bromomethyl)acrylates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              747
_journal_page_last               753
_journal_paper_doi               10.1021/jo202073n
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H25 Cl O4'
_chemical_formula_sum            'C23 H25 Cl O4'
_chemical_formula_weight         400.88
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.562(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.4209(13)
_cell_length_b                   5.6400(7)
_cell_length_c                   14.3079(16)
_cell_measurement_reflns_used    1338
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.181
_cell_measurement_theta_min      2.306
_cell_volume                     995.8(2)
_computing_cell_refinement
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite.'
_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2)'
_computing_data_reduction        'SAINT and XPREP Version 6.14, 2003'
_computing_molecular_graphics    'Bruker SHELXTL suite ver. 6.12, 2001'
_computing_publication_material  'Bruker SHELXTL suite ver. 6.12, 2001'
_computing_structure_refinement
'XL Version 2008/4 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_solution
'XS Version 2008/1 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1321
_diffrn_reflns_av_sigmaI/netI    0.1866
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11745
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.21
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 'SADABS Version 2008/1 (Sheldrick, Bruker AXS Inc.)'    
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(13)
_refine_ls_extinction_coef       0.037(3)
_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   0.905
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0242P)^2^+0.2475P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                1888
_reflns_number_total             3269
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202073n_si_002.cif
_cod_data_source_block           anc1
_cod_database_code               4026862