Asymmetric gamma-deprotonation and homoaldol reaction of 1,3-dien-2-yl carbamates: stereo- and regiochemistry.
Chedid, Roland Bou; Fröhlich, Roland; Hoppe, Dieter; Organic letters 8 (2006) 3061–3064; doi:10.1021/ol061005p

data_1506057
_publ_section_title
;
 Asymmetric gamma-deprotonation and homoaldol reaction of 1,3-dien-2-yl
 carbamates: stereo- and regiochemistry.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3061
_journal_page_last               3064
_journal_paper_doi               10.1021/ol061005p
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C27 H34 Br N O3'
_chemical_formula_weight         500.46
_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            8
_cell_length_a                   9.914(1)
_cell_length_b                   14.093(1)
_cell_length_c                   38.171(1)
_cell_measurement_reflns_used    7661
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     5333.2(7)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            27205
_diffrn_reflns_theta_full        64.71
_diffrn_reflns_theta_max         64.71
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    2.300
_exptl_absorpt_correction_T_max  0.4597
_exptl_absorpt_correction_T_min  0.3643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         8811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0665P)^2^+1.7879P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1315
_reflns_number_gt                8178
_reflns_number_total             8811
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061005psi20060524_090647.cif
_cod_data_source_block           hop3381
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1506057