Catalytic Asymmetric Intermolecular Stetter Reaction of Enals with Nitroalkenes: Enhancement of Catalytic Efficiency through Bifunctional Additives
Daniel A. DiRocco; Tomislav Rovis; Journal of the American Chemical Society 133 (2011) 10402–10405; doi:10.1021/ja203810b

data_4106385
_publ_section_title
;
 Catalytic Asymmetric Intermolecular Stetter Reaction of Enals with
 Nitroalkenes: Enhancement of Catalytic Efficiency through Bifunctional
 Additives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10402
_journal_page_last               10405
_journal_paper_doi               10.1021/ja203810b
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H20 Br N O3'
_chemical_formula_weight         366.25
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8072(3)
_cell_length_b                   12.3826(5)
_cell_length_c                   22.3700(9)
_cell_measurement_reflns_used    9483
_cell_measurement_temperature    120
_cell_measurement_theta_max      31.61
_cell_measurement_theta_min      4.28
_cell_volume                     1608.59(12)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'APEX2 (Bruker, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            43252
_diffrn_reflns_theta_full        33.31
_diffrn_reflns_theta_max         33.31
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    2.567
_exptl_absorpt_correction_T_max  0.8209
_exptl_absorpt_correction_T_min  0.5628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.320
_refine_diff_density_min         -1.802
_refine_diff_density_rms         0.454
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         6182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0936P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1594
_reflns_number_gt                5135
_reflns_number_total             6182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203810b_si_002.cif
_cod_data_source_block           rovis101_0m
_cod_database_code               4106385